Sodium borohydride → 2-(2-amino-5-hydroxymethyl-6-methylsulfanyl-pyrimidin-4-ylamino)-N-(3-trifluoromethyl-phenyl)-acetamide

HRID 1160112Notes

Reaction equation

HRID 1160112 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][C:10]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=2)=[O:11])[C:5]([CH:23]=[O:24])=[C:4]([S:25][CH3:26])[N:3]=1.[BH4-].[Na+]>CCO>[NH2:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][C:10]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:20])[F:21])[CH:14]=2)=[O:11])[C:5]([CH2:23][OH:24])=[C:4]([S:25][CH3:26])[N:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 11176608HCID 11176608, compound

Product 1

HCID 589646042-(2-amino-5-hydroxymethyl-6-methylsulfanyl-pyrimidin-4-ylamino)-N-(3-trifluoromethyl-phenyl)-acetamideYield 95.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a 25 mL round bottom flask is added 2-(2-amino-5-formyl-6-methylsulfanyl-pyrmidin-4-ylamino)-N-(3-trifluoromethyl-phenyl)-acetamide (40.0 mg, 0.10 mmol, 1.0 eq.), EtOH (2.0 mL), and sodium borohydride (5.0 mg, 0.13 mmol, 1.3 eq.). The reaction was stirred at RT for 1 hr, concentrated to remove EtOH, and partitioned between H2O and EtOAc. The aqueous layer was extracted once more with EtOAc. The combined EtOAc layers were then washed with brine, dried with Na2SO4, and concentrated to give pure 2-(2-amino-5-hydroxymethyl-6-methylsulfanyl-pyrimidin-4-ylamino)-N-(3-trifluoromethyl-phenyl)-acetamide as a white solid (37.0 mg, 95%). LC/MSD (BP Series 1100 MSD): Expected MW: 387, Observed M+H, 388.1, Retention time: 1.35 min. ANALYTICAL HPLC: >94%, Retention time: 2.82 min (8 minute run). 1H-NMR (d-MeOH): 8.00 (s, 1H), 7.78 (d, 1H), 7.50 (t, 1H), 7.39 (d, 1H), 4.62 (s, 2H), 4.38 (s, 2H), 2.42 (s, 3H) ppm.

Workup

  1. concentrationconcentrated
  2. customto remove EtOH
  3. custompartitioned between H2O and EtOAc
  4. extractionThe aqueous layer was extracted once more with EtOAc
  5. washThe combined EtOAc layers were then washed with brine
  6. dry with materialdried with Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d8ae8fc85ff140648dbab229f5328b82
Source dataset
uspto-grants-2010_10
Patent number
US07816353B2

Reaction notes

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