Benzyl Bromide → 5-(Benzyloxy)pyrimidin-2-amine

HRID 77461Notes

Reaction equation

HRID 77461 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([OH:8])=[CH:4][N:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CO>[CH2:15]([O:8][C:5]1[CH:4]=[N:3][C:2]([NH2:1])=[N:7][CH:6]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 177503882-Amino-5-hydroxypyrimidine

Product 1

HCID 207483975-(Benzyloxy)pyrimidin-2-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the solution of 2-aminopyrimidin-5-ol (0.500 g, 4.50 mmol) in dry MeOH (10 mL), K2CO3 (0.622 g, 4.50 mmol) and benzyl bromide (0.535 mL, 4.50 mmol) were added. The reaction mixture was stirred at room temperature for 18 h. Solvent was removed under reduced pressure. The residue was dissolved in ethyl acetate and washed with water and brine, then dried over sodium sulfate. The crude product was purified by flash chromatography on silica gel using 50% ethyl acetate in petroleum ether. The desired fractions were concentrated to give 5-(benzyloxy)pyrimidin-2-amine as an off-white solid (0.222 g 25%). 1HNMR 400 MHz, DMSO-d6: δ ppm 5.06 (s, 2H), 6.21 (s, 2H), 7.28-7.30 (m, 5H), 7.45 (s, 2H). LCMS: RT 1.060 min; 202.2 (M+H).

Workup

  1. customSolvent was removed under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with water and brine
  4. dry with materialdried over sodium sulfate
  5. customThe crude product was purified by flash chromatography on silica gel using 50% ethyl acetate in petroleum ether
  6. concentrationThe desired fractions were concentrated

Sources & evidence

ORD record
ord-1570080c33694f3a91eb74147028e22e
Source dataset
uspto-grants-2014_09
Patent number
US08841301B2

Reaction notes

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