Sodium borohydride → HCID 58169468, compound

HRID 1484916Notes

Reaction equation

HRID 1484916 reaction equation
[BH4-].[Na+].[CH:3]1([C:6]2[NH:10][N:9]=[C:8]([NH:11][C:12]3[C:17]([F:18])=[CH:16][N:15]=[C:14]([C:19]4[S:23][C:22]([C:24](=[O:26])[CH3:25])=[CH:21][CH:20]=4)[N:13]=3)[CH:7]=2)[CH2:5][CH2:4]1>C1COCC1.CO>[CH:3]1([C:6]2[NH:10][N:9]=[C:8]([NH:11][C:12]3[C:17]([F:18])=[CH:16][N:15]=[C:14]([C:19]4[S:23][C:22]([CH:24]([OH:26])[CH3:25])=[CH:21][CH:20]=4)[N:13]=3)[CH:7]=2)[CH2:5][CH2:4]1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 50943609HCID 50943609, compound2×

Product 1

HCID 58169468HCID 58169468, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

NaBH4 (220 mg, 5.82 mmol, 5.0 equiv.) was added to a solution of 1-(5-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-fluoropyrimidin-2-yl)thiophen-2-yl)ethanone (Compound 137) (400 mg, 1.17 mmol, 1.0 equiv.) in dry THF (10 mL) and methanol (10 mL) at 0° C. The mixture was stirred for 1 hour, quenched (crashed ice) and concentrated. The residue was recrystallized with methanol and isopropyl ether to give the racemic 1-(5-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-fluoropyrimidin-2-yl)thiophen-2-yl)ethanol (350 mg, 87%). LC-MS (m/z)=346.1 [M+H]+.

Workup

  1. customquenched (crashed ice)
  2. concentrationconcentrated
  3. customThe residue was recrystallized with methanol and isopropyl ether

Sources & evidence

ORD record
ord-b57c99da3bcf4b808fdfd1ef7a5d0972
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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