Sodium borohydride → HCID 118093033, compound

HRID 2207357Notes

Reaction equation

HRID 2207357 reaction equation
[BH4-].[Na+].[CH3:3][C:4]1[CH:5]=[C:6]([C:21]2[CH:22]=[CH:23][C:24]([C:27](=[O:29])[CH3:28])=[N:25][CH:26]=2)[CH:7]=[C:8]([NH:10][C:11]2[N:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:14]=[CH:13][N:12]=2)[CH:9]=1>O1CCCC1.CO>[CH3:3][C:4]1[CH:5]=[C:6]([C:21]2[CH:22]=[CH:23][C:24]([CH:27]([OH:29])[CH3:28])=[N:25][CH:26]=2)[CH:7]=[C:8]([NH:10][C:11]2[N:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:14]=[CH:13][N:12]=2)[CH:9]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 118092838HCID 118092838, compound

Product 1

HCID 118093033HCID 118093033, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium borohydride (46 mg, 1.2 mmol) was added to a solution of 1-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)pyridin-2-yl]ethanone (45 mg, 0.12 mmol) in tetrahydrofuran (300 μl) and methanol (300 μl) and then the reaction mixture was stirred at ambient temperature for 30 minutes. The reaction mixture was quenched with saturated aqueous potassium sodium tartrate (2 mL) and diluted with dichloromethane (3 mL). The mixture was stirred for 16 hours, filtered through a CELITE pad, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (10-40% acetone/hexanes, linear gradient) to afford 1-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)pyridin-2-yl]ethanol. MS ESI calc'd. for C19H18F3N4O [M+H]+ 375. found 375. 1H NMR (500 MHz, DMSO-d6) δ 10.26 (s, 1H), 8.82 (s, 1H), 8.71 (s, 1H), 7.98 (d, J=7.5 Hz, 1H), 7.95 (s, 1H), 7.57 (d, J=7.5 Hz, 1H), 7.54 (s, 1H), 7.27 (s, 1H), 7.18 (s, 1H), 5.39 (s, 1H), 4.80-4.72 (m, 1H), 2.35 (s, 3H), 1.38 (d, J=5.5 Hz, 3H).

Workup

  1. customThe reaction mixture was quenched with saturated aqueous potassium sodium tartrate (2 mL)
  2. additiondiluted with dichloromethane (3 mL)
  3. stirringThe mixture was stirred for 16 hours
  4. filtrationfiltered through a CELITE pad
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel chromatography (10-40% acetone/hexanes, linear gradient)

Sources & evidence

ORD record
ord-fb4ade96ebc347a6a22be6da6e8c65c1
Source dataset
uspto-grants-2016_06
Patent number
US09376418B2

Reaction notes

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