Sodium borohydride → (6-Bromo-2-methylpyrimidin-4-yl)methanol

HRID 572637Notes

Reaction equation

HRID 572637 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([C:9](OC)=[O:10])[CH:3]=1.[BH4-].[Na+]>CO>[Br:1][C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([CH2:9][OH:10])[CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86675899Methyl 6-bromo-2-methylpyrimidine-4-carboxylate

Product 1

HCID 86675898(6-Bromo-2-methylpyrimidin-4-yl)methanolYield 87.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a cold suspension of methyl 6-bromo-2-methylpyrimidine-4-carboxylate (5.4 g, 23.3 mmol, Preparation #3) in MeOH (100 mL) was added NaBH4 (1.11 g, 29.13 mmol, Spectrochem) in small portions over a period of about 45 min at about −10° C. and stirred at the same temperature for about another 30 min. The reaction was quenched with saturated ammonium chloride solution (150 mL) and the product was extracted with EtOAc (2×200 mL). The combined organic extracts were dried over sodium sulphate and concentrated under reduced pressure to afford (6-bromo-2-methylpyrimidin-4-yl)methanol 4.10 g (87.2%). 1H NMR (400 MHz, DMSO) δ: 7.56 (s, 1H), 5.72 (brs, 1H), 4.51 (d, J=3.6 Hz, 2H), 2.57 (s, 3H); MS m/z: 205(M+H)+.

Workup

  1. customThe reaction was quenched with saturated ammonium chloride solution (150 mL)
  2. extractionthe product was extracted with EtOAc (2×200 mL)
  3. dry with materialThe combined organic extracts were dried over sodium sulphate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-eb2b29172f7845fa8f3d1197ea15b380
Source dataset
uspto-grants-2015_05
Patent number
US09029409B2

Reaction notes

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