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

HRID 68302

反応式

HRID 68302 の反応式
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

参加物

4

反応物 2

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

生成物 1

HCID 2392766-Chloro-2-methylsulfanylpyrimidine-4-carboxamide収率 103.4%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

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)+.

後処理

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

出典と根拠

ORDレコード
ord-fbe7dfd91d8d45e19fc12674d442f8ad
出典データセット
uspto-grants-2014_09
特許番号
US08822451B2

関連ノート

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