Sodium borohydride → HCID 90403219, compound

HRID 2200656Notes

Reaction equation

HRID 2200656 reaction equation
[Cl:1][C:2]1[CH:38]=[CH:37][C:5]([CH2:6][N:7]2[C:15]3[C:14](=[O:16])[N:13]([CH2:17][CH2:18][C:19](=[O:22])[CH2:20][CH3:21])[C:12](=[O:23])[N:11]([CH3:24])[C:10]=3[N:9]=[C:8]2[O:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([O:32][C:33]([F:36])([F:35])[F:34])[CH:27]=2)=[CH:4][CH:3]=1.[BH4-].[Na+]>CO.C(OCC)(=O)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:15]3[C:14](=[O:16])[N:13]([CH2:17][CH2:18][CH:19]([OH:22])[CH2:20][CH3:21])[C:12](=[O:23])[N:11]([CH3:24])[C:10]=3[N:9]=[C:8]2[O:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([O:32][C:33]([F:36])([F:34])[F:35])[CH:27]=2)=[CH:37][CH:38]=1

Participants

6

Reactant 2

HCID 4311764Sodium borohydrideHCID 90402350HCID 90402350, compound

Product 1

HCID 90403219HCID 90403219, compoundYield 33.5%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 7-(4-chlorobenzyl)-3-methyl-1-(3-oxopentyl)-8-(3-(trifluoromethoxy)phenoxy)-1H-purine-2,6(3H,7H)-dione (150 mg, 0.273 mmol, example 20) in methanol (20 mL) was added sodium borohydride (40 mg, 1.05 mmol) at 0° C. under nitrogen. The mixture was stirred at 0° C. for 2 h. The mixture was diluted with ethyl acetate and water, and the phases were separated. The organic phase was washed with brine, dried over sodium sulfate, filtered and concentrated. The crude product was purified by preparative HPLC to give 7-(4-chlorobenzyl)-1-(3-hydroxypentyl)-3-methyl-8-(3-(trifluoromethoxy)phenoxy)-1H-purine-2,6(3H,7H)-dione (50 mg, 33.5% yield) as white solid. 1H-NMR (DMSO-d6) δ 7.63-7.58(t, 1H), 7.49(s, 1H), 7.44-7.42(m, 5H), 7.34-7.31(d, 1H), 5.44(s, 2H), 4.48-4.46(d, 1H), 4.08-4.01(m, 1H), 3.89-3.83(m, 1H), 3.42-3.37(m, 1H), 3.29(s, 3H), 1.63-1.55(m, 2H), 1.44-1.31(m, 2H), 0.87-0.84(t, 3H). LCMS retention time 3.372 min; LCMS MH+ 553.

Workup

  1. customthe phases were separated
  2. washThe organic phase was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-e4f9e05fe8124027b95e768935d07cd3
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

Loading…