Sodium borohydride → HCID 66970299, compound

HRID 1365899Notes

Reaction equation

HRID 1365899 reaction equation
[BH4-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][CH2:13][CH:12]([C:16]([NH:18][C:19]2[CH:20]=[C:21]([C:25]3[CH:30]=[C:29]([N:31]4[CH2:36][CH2:35][O:34][CH2:33][CH2:32]4)[N:28]=[C:27]([C:37]4[O:38][C:39]([CH:42]=[O:43])=[CH:40][CH:41]=4)[N:26]=3)[CH:22]=[CH:23][CH:24]=2)=[O:17])[CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4]>C(O)C>[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][CH2:13][CH:12]([C:16]([NH:18][C:19]2[CH:20]=[C:21]([C:25]3[CH:30]=[C:29]([N:31]4[CH2:32][CH2:33][O:34][CH2:35][CH2:36]4)[N:28]=[C:27]([C:37]4[O:38][C:39]([CH2:42][OH:43])=[CH:40][CH:41]=4)[N:26]=3)[CH:22]=[CH:23][CH:24]=2)=[O:17])[CH2:11]1)=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86630891HCID 86630891, compound

Product 1

HCID 66970299HCID 66970299, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (0.076 g) was added portionwise to a mixture of 4-[3-(1-tert-butoxycarbonylpiperidin-3-ylcarbonylamino)phenyl]-2-(5-formylfuran-2-yl)-6-morpholinopyrimidine (0.112 g) and ethanol (5 ml) and the reaction mixture was stirred at ambient temperature for 3 hours. The mixture was evaporated to give 4-[3-(1-tert-butoxycarbonylpiperidin-3-ylcarbonylamino)phenyl]-2-(5-hydroxymethylfuran-2-yl)-6-morpholinopyrimidine which was used without further purification. A mixture of the material so obtained, trifluoroacetic acid (1.5 ml) and methylene chloride (2.5 ml) was stirred at ambient temperature for 1 hour and then heated to 40° C. for 10 minutes. The mixture was evaporated and the residue was partitioned between methylene chloride and water. The aqueous layer was separated, basified by the addition of aqueous ammonium hydroxide (d=0.88) and extracted with methylene chloride. The organic extracts were combined, dried over magnesium sulphate and evaporated. The residue was purified by HPLC using a Waters ‘Xterra’ preparative reversed-phase column (5 microns silica, 19 mm diameter, 100 mm length) using decreasingly polar mixtures of water [containing 1% aqueous ammonium hydroxide (d=0.88)] and acetonitrile as eluent. There was thus obtained the title compound as a solid (4.4 mg); NMR Spectrum: (CD3OD) 1.47-1.58 (m, 1H), 1.64-1.75 (m, 2H), 1.91-1.97 (m, 1H), 2.5-2.65 (m, 2H), 2.82 (m, 1H), 2.9-2.94 (m, 1H), 3.07 (m, 1H), 3.17-3.28 (m, 8H), 4.53 (s, 2H), 6.38 (d, 1H), 6.85 (s, 1H), 7.15 (d, 1H), 7.34 (t, 1H), 7.6 (d, 1H), 7.69 (d, 1H), 8.16 (s, 1H); Mass Spectrum: M+H+ 464.

Workup

  1. customThe mixture was evaporated

Sources & evidence

ORD record
ord-fb4b0b0a85be4bd8be69c37b2c615369
Source dataset
uspto-grants-2011_02
Patent number
US07893063B2

Reaction notes

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