Sodium borohydride → HCID 46893519, compound

HRID 1424474Notes

Reaction equation

HRID 1424474 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([C:11]2[N:20]=[C:19]([NH:21][C:22]3[CH:26]=[C:25]([CH3:27])[NH:24][N:23]=3)[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]=2)=[O:10])[CH:5]=[CH:6][C:7]=1[F:8].[BH4-].[Na+]>CO.C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([C:11]2[N:20]=[C:19]([NH:21][C:22]3[CH:26]=[C:25]([CH3:27])[NH:24][N:23]=3)[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]=2)[OH:10])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 66613915HCID 66613915, compound

Product 1

HCID 46893519HCID 46893519, compoundYield 9.1%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To crude (3-chloro-4-fluorophenyl)(4-(5-methyl-1H-pyrazol-3-ylamino)quinazolin-2-yl)methanone (458 mg, 1.2 mmol) in 1:1 MeOH/THF (60 mL) at 0° C. was added sodium borohydride (0.048 g, 1.3 mmol), and the solution was stirred for 30 min. The reaction was quenched by addition of 6 N HCl and the mixture was concentrated to dryness. The residue was purified by silica gel chromatography eluting with 0-15% MeOH/DCM. The resulting solid was triturated with methanol to afford (3-chloro-4-fluorophenyl)(4-(5-methyl-1H-pyrazol-3-ylamino)quinazolin-2-yl)methanol (42 mg). 1H NMR (300 MHz, DMSO-d6) δ 2.27 (s, 3H) 5.70 (s, 1H) 6.01 (s, 1H) 6.41 (s, 1H) 7.36 (t, 1H) 7.47-7.52 (m, 2H) 7.79-7.82 (m, 3H) 8.59 (d, 1H) 10.42 (bs, 1H) 12.16 (bs, 1H); LC-MS (ESI) m/z 384 (M+H)+.

Workup

  1. customThe reaction was quenched by addition of 6 N HCl
  2. concentrationthe mixture was concentrated to dryness
  3. customThe residue was purified by silica gel chromatography
  4. washeluting with 0-15% MeOH/DCM
  5. customThe resulting solid was triturated with methanol

Sources & evidence

ORD record
ord-232d0db262ea4c1283e6d3af3eba7435
Source dataset
uspto-grants-2015_01
Patent number
US08927711B2

Reaction notes

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