2-Chloro-4-(Cyclopropylamino)Pyrimidine-5-Carboxylic Acid synthesis
- Product Name:2-Chloro-4-(Cyclopropylamino)Pyrimidine-5-Carboxylic Acid
- CAS Number:1192711-37-7
- Molecular formula:C8H8ClN3O2
- Molecular Weight:213.62
1192711-36-6
1192711-37-7
The general procedure for the synthesis of 2-chloro-4-(cyclopropylamino)pyrimidine-5-carboxylic acid using the compound (CAS:1192711-36-6) as a starting material was as follows: first, ethyl ester 1.5 (6.02 g, 24 mmol) was dissolved in 1,4-dioxane (26 mL), followed by the addition of an aqueous lithium hydroxide solution (1.0 M, 26 mL, 26 mmol). The reaction mixture was stirred at room temperature until all starting materials were completely converted to carboxylic acids. Next, the reaction mixture was diluted with water to a total volume of 100 mL and acidified with 6 M hydrochloric acid to pH=2. After acidification, the solids in the resulting suspension were collected by filtration and dried by suction drying to give 3.51 g of the carboxylic acid product in 64% yield. The structure of the product was confirmed by 1H NMR (DMSO-d6, 400 MHz) with chemical shifts of δ 8.64 (d, 1H), 8.74 (s, 1H), 4.50 (m, 1H), 2.31 (m, 2H), 2.03 (m, 2H), 1.72 (m, 2H), respectively.
1192711-36-6
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1192711-37-7
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Yield:1192711-37-7 64%
Reaction Conditions:
Stage #1: ethyl 2-chloro-4-(cyclopropylamino)pyrimidine-5-carboxylatewith water;lithium hydroxide in 1,4-dioxane at 20;
Stage #2: with hydrogenchloride in 1,4-dioxane;water; pH=2;
Steps:
5.5
Ethyl ester 1.5 (6.02g, 24 mmol) was diluted with 1,4-dioxane (26 mL) followed by aqueous lithium hydroxide (1.0 M, 26 mL, 26 mmol) and stirred at rt until all starting material had been converted to the carboxylic acid. The reaction was then diluted with water to a total volume of 100 mL and acidified to pH = 2 with 6 M HCl. The resulting suspension was then filtered and dried by aspiration giving 3.5 Ig of the carboxylic acid (64%). 1H NMR (DMSOd6, 400 MHz): δ 8.64 (d, IH), 8.74 (s, IH), 4.50 (m, IH), 2.31 (m, 2H), 2.03 (m, 2H), 1.72 (m, 2H).
References:
WO2009/131687,2009,A2 Location in patent:Page/Page column 102
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1192711-37-7
25 suppliers
$109.00/100mg