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

HRID 269850Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 269850
[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

Komponenten

5

Edukt 3

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

Produkt 1

HCID 101723842-(Tetrahydropyran-4-ylamino)-6-[(2-fluorophenyl)hydroxylmethyl]thieno[2,3-d]pyrimidineAusbeute 46,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-166fda0c2d2b49e1ae643836c44010b9
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07449472B2

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