Tetrahydrofuran → 1-(2-Isopropylamino-6-methyl-pyrimidin-4-yl)-ethanone

HRID 2069468ノート

反応式

HRID 2069468 の反応式
CON(C)[C:4]([C:6]1[CH:11]=[C:10]([CH3:12])[N:9]=[C:8]([NH:13][CH:14]([CH3:16])[CH3:15])[N:7]=1)=[O:5].[CH2:18]1COCC1>C[Mg]Br.CCOCC>[CH:14]([NH:13][C:8]1[N:7]=[C:6]([C:4](=[O:5])[CH3:18])[CH:11]=[C:10]([CH3:12])[N:9]=1)([CH3:15])[CH3:16]

参加物

5

反応物 2

HCID 8028TetrahydrofuranHCID 866453112-Isopropylamino-6-methyl-pyrimidine-4-carboxylic acid methoxy-methyl-amide

生成物 1

HCID 685106621-(2-Isopropylamino-6-methyl-pyrimidin-4-yl)-ethanone

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 178418573HCID 178418573、化合物溶媒

反応条件

温度
5 °C

実験手順

To a solution of 2-isopropylamino-6-methyl-pyrimidine-4-carboxylic acid methoxy-methyl-amide (2.39 g, 10.0 mmol) in THF (50 mL), methyl magnesium bromide (7.0 mL of a 3 M solution in ether, 20.1 mmol) is added dropwise at 5° C. The mixture is stirred at 5° C. for 1.5 h. The reaction is quenched by adding NH4Cl. The mixture is diluted with EtOAc (75 mL), washed with sat. aq. NaHCO3, dried over Na2SO4, filtered and concentrated to give 1-(2-isopropylamino-6-methyl-pyrimidin-4-yl)-ethanone (1.71 g) as a yellow solid. LC-MS: tR=0.75 min, [M+H]+=194.01; 1H NMR (CDCl3): δ 1.29 (d, J=6.5 Hz, 6H), 2.41 (s, 3H), 2.62 (s, 3H), 4.22 (m, 1H), 5.02 (m, 1H), 6.97 (s, 1H).

後処理

  1. customThe reaction is quenched
  2. additionby adding NH4Cl
  3. additionThe mixture is diluted with EtOAc (75 mL)
  4. washwashed with sat. aq. NaHCO3
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-6bc4ff87e12b43aa97e52f9ab50c5571
出典データセット
uspto-grants-2012_10
特許番号
US08299086B2

反応ノート

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