4,6-Dichloro-pyrimidine-5-carbonyl chloride → methyl 2-(4-(4-(N-(2-(tert-butyldimethylsilyloxy) ethyl)-4,6-dichloropyrimidine-5-carboxamido)-3-fluorophenyl)cyclohexyl)acetate

HRID 2237622ノート

反応式

HRID 2237622 の反応式
[Cl:1][C:2]1[C:7]([C:8](Cl)=[O:9])=[C:6]([Cl:11])[N:5]=[CH:4][N:3]=1.[Si:12]([O:19][CH2:20][CH2:21][NH:22][C:23]1[CH:28]=[CH:27][C:26]([CH:29]2[CH2:34][CH2:33][CH:32]([CH2:35][C:36]([O:38][CH3:39])=[O:37])[CH2:31][CH2:30]2)=[CH:25][C:24]=1[F:40])([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13]>C1COCC1>[Si:12]([O:19][CH2:20][CH2:21][N:22]([C:23]1[CH:28]=[CH:27][C:26]([CH:29]2[CH2:34][CH2:33][CH:32]([CH2:35][C:36]([O:38][CH3:39])=[O:37])[CH2:31][CH2:30]2)=[CH:25][C:24]=1[F:40])[C:8]([C:7]1[C:6]([Cl:11])=[N:5][CH:4]=[N:3][C:2]=1[Cl:1])=[O:9])([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13]

参加物

4

反応物 2

HCID 121633604,6-Dichloro-pyrimidine-5-carbonyl chlorideHCID 59302498HCID 59302498、化合物

生成物 1

HCID 59302507methyl 2-(4-(4-(N-(2-(tert-butyldimethylsilyloxy) ethyl)-4,6-dichloropyrimidine-5-carboxamido)-3-fluorophenyl)cyclohexyl)acetate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of 4,6-dichloropyrimidine-5-carbonyl chloride (82.5 mg, 0.390), methyl 2-(4-(4-(2-(tert-butyldimethylsilyloxy)ethylamino)-3-fluorophenyl)cyclohexyl)acetate (110 mg, 0.26 mmol) and TEA (0.054 mL, 0.39 mmol) in THF (2 mL) was stirred at room temperature under nitrogen for 14 hours. The reaction mixture was concentrated to remove THF. The residue was diluted with EtOAc, washed with water, dried over MgSO4 and concentrated. The crude material was purified by a 12 g silica gel column eluted with 3-15% EtOAc in heptane to give methyl 2-(4-(4-(N-(2-(tert-butyldimethylsilyloxy) ethyl)-4,6-dichloropyrimidine-5-carboxamido)-3-fluorophenyl)cyclohexyl)acetate a colorless oil (60 mg). m/z=598.2 (M+1).

後処理

  1. concentrationThe reaction mixture was concentrated
  2. customto remove THF
  3. additionThe residue was diluted with EtOAc
  4. washwashed with water
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe crude material was purified by a 12 g silica gel column
  8. washeluted with 3-15% EtOAc in heptane

出典と根拠

ORDレコード
ord-973ea8da1c4f4e66839b858e6c877a31
出典データセット
uspto-grants-2010_05
特許番号
US07718645B2

反応ノート

読み込み中…