Methanol → HCID 18323774, compound

HRID 1872056Notes

Reaction equation

HRID 1872056 reaction equation
[BH4-].[Na+].[Br:3][C:4]1[CH:9]=[C:8]([CH:10]([CH3:12])[CH3:11])[CH:7]=[CH:6][C:5]=1[N:13]([CH2:29][CH3:30])[C:14]1[N:19]=[C:18]([C:20]([C:22]2[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=2)=[O:21])[CH:17]=[C:16]([CH3:28])[N:15]=1.C(Cl)(Cl)Cl.CO>C(O)C>[Br:3][C:4]1[CH:9]=[C:8]([CH:10]([CH3:12])[CH3:11])[CH:7]=[CH:6][C:5]=1[N:13]([CH2:29][CH3:30])[C:14]1[N:19]=[C:18]([CH:20]([OH:21])[C:22]2[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=2)[CH:17]=[C:16]([CH3:28])[N:15]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 6212ChloroformHCID 4311764Sodium borohydrideHCID 18323702HCID 18323702, compound

Product 1

HCID 18323774HCID 18323774, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (0.11 g, 2.8 mmol) was added to a solution of N-(2-bromo-4-(1-methylethyl)phenyl)-N-ethyl-4-(3-pyridylcarbonyl)-6-methylpyrimidinamine (0.6 g, 1.4 mmol) in ethanol (5 mL). After being stirred for 71 h, the reaction mixture was concentrated in vacuo, treated with a 1N NaOH solution and extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated in vacuo to give a colorless oil. Column chromatography (chloroform:methanol::9:1) afforded the title product as an oil (600 mg, 96% yield, Rf 0.4): NMR (CDCl3, 300 MHz): 8.65-8.45 (m, 2H), 7.55 (br s, 2H), 7.3-7.1 (m, 2H), 6.25-6.15 (m, 1H), 5.7-5.5 (m, 0.5H), 5.45-5.3 (m, 0.5H), 5.15-4.95 (m, 1H), 4.3-4.1 (m, 1H), 3.9-3.7 (m, 1H), 3.0-2.85 (m, 1H), 2.45-2.2 (m, 3H), 2.3-2.2 (m, 1H), 1.35-1.2 (m, 9H); CI-HRMS: Calcd (C22H25BrN4O): 441.1290 (M+H), Found: 441.1274.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. additiontreated with a 1N NaOH solution
  3. extractionextracted three times with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give a colorless oil

Sources & evidence

ORD record
ord-cc2bfc9b4a3b43ec94d52a0583b721af
Source dataset
uspto-grants-2000_08
Patent number
US06107301

Reaction notes

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