Methanol → HCID 11668197, compound

HRID 216108Notes

Reaction equation

HRID 216108 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[CH2:9][CH2:10][NH:11][C:12]1[N:17]=[C:16]([O:18][CH3:19])[N:15]=[C:14]([C:20]2[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=2)[CH:23]=[O:24])[CH:13]=1.CO.[BH4-].[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[CH2:9][CH2:10][NH:11][C:12]1[N:17]=[C:16]([O:18][CH3:19])[N:15]=[C:14]([C:20]2[CH:21]=[C:22]([CH2:23][OH:24])[CH:25]=[CH:26][CH:27]=2)[CH:13]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 53321837HCID 53321837, compound

Product 1

HCID 11668197HCID 11668197, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-{6-[2-(2-chloro-6-fluoro-phenyl)-ethylamino]-2-methoxy-pyrimidin-4-yl}-benzaldehyde [150 mg, 0.39 mmol, Example 35(v)], in DCM (4 mL) and MeOH (1 mL) is treated with sodium borohydride (74 mg, 1.95 mmol) at 0° C. After 1 hour at 20° C., the mixture is concentrated, and extracted twice with EtOAc (10 mL). The combined extracts are dried over magnesium sulfate and filtered through a plug of silica to afford (3-{6-[2-(2-chloro-6-fluoro-phenyl)-ethylamino]-2-methoxy-pyrimidin-4-yl}-phenyl)-methanol [110 mg, 73%, Example 9(d)]. LCMS: RT=2.79 minutes, MS: 388 (M+H). IC50=2.4 nM

Workup

  1. concentrationthe mixture is concentrated
  2. extractionextracted twice with EtOAc (10 mL)
  3. dry with materialThe combined extracts are dried over magnesium sulfate
  4. filtrationfiltered through a plug of silica

Sources & evidence

ORD record
ord-48950a0483da403eb0827add1ff34739
Source dataset
uspto-grants-2012_06
Patent number
US08193183B2

Reaction notes

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