Sodium borohydride → HCID 58603723, compound

HRID 14836Notes

Reaction equation

HRID 14836 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][C:11]2[N:16]=[C:15]([C:17]3[CH:18]=[C:19]([C:23](=[O:25])[CH3:24])[CH:20]=[CH:21][CH:22]=3)[CH:14]=[CH:13][N:12]=2)=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[OH:25][CH:23]([C:19]1[CH:18]=[C:17]([C:15]2[CH:14]=[CH:13][N:12]=[C:11]([NH:10][CH2:9][CH2:8][C:5]3[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=3)[N:16]=2)[CH:22]=[CH:21][CH:20]=1)[CH3:24]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 670446891-(3-{2-[2-(4-Hydroxy-phenyl)-ethylamino]-pyrimidin-4-yl}-phenyl)-ethanone

Product 1

HCID 58603723HCID 58603723, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Intermediate 62 (0.96 g) was dissolved in methanol (30 mL) and treated with 0.5 g of sodium borohydride. The solvent was removed and the residue partitioned between ethyl acetate and water. The residue was purified by HPLC. LC-MS showed the product had the expected M+H+ of 336. 1H NMR (Varian 300 MHz, CDCl3, shifts relative to the solvent peak at 7.24 ppm) δ 8.31 (m, 1H) 8.05 (s, 1H) 7.4-7.6 (m, 3H) 7.09 (d, 2H) 6.99 (d, 1H) 6.72 (d, 2H) 5.29 (t, 1H) δ 5.0 (q, 1H) 3.73 (q, 2H) 2.9 (t, 2H) 1.52 (d, 3H).

Workup

  1. customThe solvent was removed
  2. customthe residue partitioned between ethyl acetate and water
  3. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-358656414a43416d841bb50314efb1ba
Source dataset
uspto-grants-2010_06
Patent number
US07732444B2

Reaction notes

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