4-Chloro-2-(methylthio)pyrimidine-5-carboxylic acid ethyl ester → HCID 849409、化合物

HRID 2251084ノート

反応式

HRID 2251084 の反応式
[CH2:1]([O:3][C:4]([C:6]1[C:7](Cl)=[N:8][C:9]([S:12][CH3:13])=[N:10][CH:11]=1)=[O:5])[CH3:2].[NH2:15][C:16]1[N:20]([CH3:21])[N:19]=[C:18]([CH3:22])[CH:17]=1>C(O)C>[CH2:1]([O:3][C:4]([C:6]1[C:7]([NH:15][C:16]2[N:20]([CH3:21])[N:19]=[C:18]([CH3:22])[CH:17]=2)=[N:8][C:9]([S:12][CH3:13])=[N:10][CH:11]=1)=[O:5])[CH3:2]

参加物

4

反応物 2

HCID 800084-Chloro-2-(methylthio)pyrimidine-5-carboxylic acid ethyl esterHCID 5207211,3-Dimethyl-1H-pyrazol-5-amine

生成物 1

HCID 849409HCID 849409、化合物収率 79.7%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
80 °C

実験手順

To a solution of 4-chloro-2-methylsulfanyl-pyrimidine-5-carboxylic acid ethyl ester (4.6 g, 19.6 mmol) in ethanol (90 mL) is added 5-amino-1,3-dimethylpyrazole (4.4 g, 39.2 mmol). The mixture is heated for 22 hours at 80° C. The reaction is cooled to room temp and concentrated in vacuo. The solid which remains is dissolved in CHCl3 and washed with aqueous saturated NaHCO3 solution. The organic phase is dried (MgSO4), filtered and concentrated in vacuo and the resulting residue is purified over silica (50% EtOAc//hexanes, followed by 100% EtOAc) to afford 4.8 g of the desired product: 1H NMR (300 MHz, CDCl3) δ10.29 (s, NH), 8.82 (s, 1H), 6.30 (s, 1H), 4.43 (q, J=7.2 Hz, 2H), 3.77 (s, 3H), 2.53 (s, 3H), 2.30 (s, 3H), 1.45 (t, J=7.2 Hz, 3H); ESI+ MS: m/z (rel intensity) 308.0 (100, M++H).

後処理

  1. temperatureThe reaction is cooled to room temp
  2. concentrationconcentrated in vacuo
  3. dissolutionThe solid which remains is dissolved in CHCl3
  4. washwashed with aqueous saturated NaHCO3 solution
  5. dry with materialThe organic phase is dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customthe resulting residue is purified over silica (50% EtOAc//hexanes, followed by 100% EtOAc)

出典と根拠

ORDレコード
ord-448fe476ba9c4e8db6c2440cfb53c2bf
出典データセット
uspto-grants-2008_01
特許番号
US07319102B1

反応ノート

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