Sodium borohydride → HCID 90402777, compound

HRID 2200704Notes

Reaction equation

HRID 2200704 reaction equation
[Cl:1][C:2]1[CH:37]=[CH:36][C:5]([CH2:6][N:7]2[C:15]3[C:14](=[O:16])[N:13]([CH2:17][CH2:18][CH2:19][OH:20])[C:12](=[O:21])[N:11]([CH3:22])[C:10]=3[N:9]=[C:8]2[C:23](=[O:35])[C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([O:30][C:31]([F:34])([F:33])[F:32])[CH:25]=2)=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:37]=[CH:36][C:5]([CH2:6][N:7]2[C:15]3[C:14](=[O:16])[N:13]([CH2:17][CH2:18][CH2:19][OH:20])[C:12](=[O:21])[N:11]([CH3:22])[C:10]=3[N:9]=[C:8]2[CH:23]([OH:35])[C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([O:30][C:31]([F:32])([F:33])[F:34])[CH:25]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 90402688HCID 90402688, compound

Product 1

HCID 90402777HCID 90402777, compoundYield 22.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 7-(4-chlorobenzyl)-1-(3-hydroxypropyl)-3-methyl-8-(3-(trifluoromethoxy)benzoyl)-1H-purine-2,6(3H,7H)-dione (50 mg, 0.081 mmol, example 91) in methanol (3 mL) was added sodium borohydride (10 mg, 0.263 mmol) at 0° C. under nitrogen. The reaction was stirred at 0° C. for 2 h. The reaction was quenched and partitioned with ethyl acetate and water. The organic phase was washed with brine, dried over sodium sulfate, filtered and concentrated to give a crude product, which was purified by preparative HPLC to give 7-(4-chlorobenzyl)-8-(hydroxy(3-(trifluoromethoxy)phenyl)methyl)-1-(3-hydroxypropyl)-3-methyl-1H-purine-2,6(3H,7H)-dione (10 mg, 22.9%) as white solid. 1H-NMR (CDCl3) δ 7.36-7.31(t, 1H), 7.23-7.14(m, 5H), 6.94-6.92(d, 2H), 5.87-5.85(d, 1H), 5.60-5.56(d, 1H), 5.39-5.35(d, 1H), 4.20-4.17(t, 2H), 3.65-3.63(s, 4H), 3.54-3.51(m, 2H), 3.31(s, 1H), 1.91-1.88(t, 2H). LCMS retention time 2.605 min; LCMS MH+ 539.

Workup

  1. customThe reaction was quenched
  2. custompartitioned with ethyl acetate and water
  3. washThe organic phase was washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a crude product, which
  8. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-1d33aab136c44db7bce181cb9d7a8871
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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