Ammonia → 6-Chloro-2-methylsulfanylpyrimidine-4-carboxamide

HRID 68302

Reaction equation

HRID 68302 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[C:9]([Cl:11])[N:8]=[C:7]([S:12][CH3:13])[N:6]=1)=O.[NH3:14]>C(Cl)(Cl)Cl>[Cl:11][C:9]1[N:8]=[C:7]([S:12][CH3:13])[N:6]=[C:5]([C:3]([NH2:14])=[O:2])[CH:10]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 238726Methyl 6-chloro-2-(methylsulfanyl)pyrimidine-4-carboxylate

Product 1

HCID 2392766-Chloro-2-methylsulfanylpyrimidine-4-carboxamideYield 103.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A 500 mL flask was charged with the 6-chloro-2-methylsulfanyl-pyrimidine-4-carboxylic acid methyl ester (4.37 g, 20 mmol), and chloroform (30 mL). Ammonia (57 mL, 7 M in methanol, 0.4 mol, 20 eq.) was added with stirring. HPLC analysis after 20 minutes indicated no starting methyl ester remained. The mixture was sparged with nitrogen for 30 min, then concentrated in vacuo, and dried under high vacuum to afford the 6-chloro-2-methylsulfanyl-pyrimidine-4-carboxylic acid amide (4.21 g, quant.) in sufficient purity for use in the next step. 1H NMR (500 MHz, CDCl3) □ 7.76 (s, 1H), 7.60 (br s, 1H), 5.97 (br s, 1H), 2.61 (s, 3H); ESI-MS m/z 204.1 (M+H)+.

Workup

  1. customThe mixture was sparged with nitrogen for 30 min
  2. concentrationconcentrated in vacuo
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-fbe7dfd91d8d45e19fc12674d442f8ad
Source dataset
uspto-grants-2014_09
Patent number
US08822451B2

Linked notes

Loading…