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 2237622노트

반응식

HRID 2237622 반응식
[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]

참가 물질

4

반응물 2

HCID 121633604,6-Dichloro-pyrimidine-5-carbonyl chlorideHCID 59302498HCID 59302498, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-973ea8da1c4f4e66839b858e6c877a31
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07718645B2

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