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Process for the preparation of 2-amino-5,8-dimethoxy[1,2,4]triazolo[1,5-c]pyrimidine from 4-chloro-2,5-dimethoxypyrimidine

A technology of triazolo and 5-c, which is applied in the preparation of intermediates of sulfonamide herbicides, 01] This application provides a 4-field, which can solve the problems of high irritation and toxicity of cyanogen halides

Inactive Publication Date: 2015-07-08
DOW AGROSCIENCES LLC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Cyanogen halides are highly irritating and very toxic

Method used

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  • Process for the preparation of 2-amino-5,8-dimethoxy[1,2,4]triazolo[1,5-c]pyrimidine from 4-chloro-2,5-dimethoxypyrimidine
  • Process for the preparation of 2-amino-5,8-dimethoxy[1,2,4]triazolo[1,5-c]pyrimidine from 4-chloro-2,5-dimethoxypyrimidine
  • Process for the preparation of 2-amino-5,8-dimethoxy[1,2,4]triazolo[1,5-c]pyrimidine from 4-chloro-2,5-dimethoxypyrimidine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Example 1.Preparation of 2,5-dimethoxy-4-cyanoaminopyrimidine (2)

[0042] Step a:

[0043]

[0044] 7.8 grams (g) (121.53 millimoles (mmol)) of sodium cyanamide hydrogen and 34.2 g of N-methyl-2-pyrrolidone (NMP) were successively added to a 100 milliliter (mL) three-necked round-bottomed flask at one time, and the The slurry mixture was cooled in a water bath at ambient temperature. To this mixture was added 10.0 g (54.99 mmol) of 96% 4-chloro-2,5-dimethoxypyrimidine (1; CDMP) in one portion. The mixture was stirred at ambient temperature (1 H NMR (DMSO-d 6 , 400MHz) δ3.72(s, 3H), 3.94(s, 3H), 7.46(s, 1H), 12.48(br s, ~1H); 13 C NMR (DMSO, 100 MHz) δ 55.21, 56.60, 116.20, 121.8 (br s), 138.9, 153.9, 162.6 (br s).

Embodiment 2

[0045] Example 2. Preparation of 2,5-dimethoxy-4-cyanoaminopyrimidine (2)

[0046] Step a:

[0047]

[0048] In a 100mL three-necked round bottom flask, 7.8g (121.53mmol)) of sodium cyanamide hydrogen and 34.2g of N-methyl-2-pyrrolidone (NMP) were successively added at one time, and the slurry mixture was cooled in a water bath at ambient temperature . To this mixture was added 10.0 g (54.99 mmol) of 96% 4-chloro-2,5-dimethoxypyrimidine (1; CDMP) in one portion. The mixture was stirred at ambient temperature (1 H and 13 The C NMR spectrum is the same as reported in Example 1.

Embodiment 3

[0049] Example 3. Preparation of 2,5-dimethoxy-4-cyanoaminopyrimidine (2)

[0050] Step a:

[0051]

[0052] 4-Chloro-2,5-dimethoxypyrimidine (CDMP; 15 g, 0.086 mol) was dissolved in N-methyl-2-pyrrolidone (NMP; 62.5 g) at ambient temperature. Sodium cyanamide hydrogen (12.1 g, 2.2 eq) was added in one portion and the mixture was heated to 50° C. while stirring for 2.5 h. The resulting slurry was cooled to 25°C and 150 mL of water was added. Concentrated hydrochloric acid was added dropwise until the pH reached 5.5. The thick slurry was filtered and washed twice with 10 mL of water to give 2,5-dimethoxy-4-cyanoamino-pyrimidine (2) (11.83 g, 76% yield) as a white solid.

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Abstract

2-Amino-5,8-dialkoxy[1,2,4]-triazolo[1,5-c]pyrimidines are manufactured from 4-chloro-2,5-dialkoxypyrimidines in a process that avoids hydrazine and cyanogen halide.

Description

Background technique [0001] The application provides preparation of 2-amino-5,8-dimethoxy[1,2,4]triazolo[1,5-c]pyrimidine from 4-chloro-2,5-dimethoxypyrimidine method. [0002] U.S. Patent 6,005,108 describes certain substituted 2-amino-5,8-dialkoxy[1,2,4]-triazolo[1,5-c]pyrimidine compounds and their use as compounds for the preparation of sulfonamide herbicides Use of intermediates. 2-Amino-5,8-dimethoxy[1,2,4]triazolo[1,5-c]pyrimidine is a useful intermediate for the preparation of penoxsulam. Monatsh. Chem. 1983, 114, 789 describes the preparation of certain (amino)thiocarbonyl carbamates, which are then reacted with hydroxylamine and then cyclized to [1,2,4]triazolo[1,5- a] pyrimidin-2-amine. WO 2009 / 047514 A1 describes the preparation of certain (amino)thiocarbonyl carbamates and their subsequent reaction with hydroxylamine followed by cyclization to [1,2,4]triazolo[1,5-a]pyridine and [1,2,4]triazolo[1,5-c]pyrimidine compounds. US 6,559,101 B2 describes the prepara...

Claims

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Application Information

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IPC IPC(8): C07D487/00
CPCC07D487/04C07D239/52C08F4/651C08F4/657C08F10/06
Inventor D·C·布兰德G·罗思C·博特C·T·哈密尔顿J·纽曼
Owner DOW AGROSCIENCES LLC
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