Ethyl Acetate → 2-(Tetrahydropyran-4-ylamino)-6-[(2-fluorophenyl)hydroxylmethyl]thieno[2,3-d]pyrimidine

HRID 9761노트

반응식

HRID 9761 반응식
[O:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8]2[N:9]=[CH:10][C:11]3[CH:16]=[C:15]([C:17](=[O:25])[C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[F:24])[S:14][C:12]=3[N:13]=2)[CH2:3][CH2:2]1.[BH4-].[Na+].C(OCC)(=O)C>C(O)C>[O:1]1[CH2:2][CH2:3][CH:4]([NH:7][C:8]2[N:9]=[CH:10][C:11]3[CH:16]=[C:15]([CH:17]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[F:24])[OH:25])[S:14][C:12]=3[N:13]=2)[CH2:5][CH2:6]1

참가 물질

5

반응물 3

HCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 102155492-(Tetrahydropyran-4-ylamino)-6-(2-fluorobenzoyl)thieno[2,3-d]pyrimidine

생성물 1

HCID 101723842-(Tetrahydropyran-4-ylamino)-6-[(2-fluorophenyl)hydroxylmethyl]thieno[2,3-d]pyrimidine수율 46.4%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a solution of 2-(tetrahydropyran-4-ylamino)-6-(2-fluorobenzoyl)thieno[2,3-d]pyrimidine (300 mg) in ethanol (30 mL) was added sodium borohydride (0.4 g) at room temperature and stirred overnight. Ethyl acetate (50 mL) was added to the reaction mixture. The organic layer was separated, washed with brine, dried, and evaporated. Purification by preparative TLC (silica gel, 50% EtOAc/hexanes) gave 140 mg of the alcohol. MS: 360.2 (M+H).

후처리

  1. customThe organic layer was separated
  2. washwashed with brine
  3. customdried
  4. customevaporated
  5. customPurification by preparative TLC (silica gel, 50% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-933511404d6d45dc844e54a6435270b8
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091347B2

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