Benzyl Bromide → 3-Benzyl-6-(methylamino)pyrimidin-4(3H)-one

HRID 2067744Notes

Reaction equation

HRID 2067744 reaction equation
[CH3:1][NH:2][C:3]1[N:8]=[CH:7][NH:6][C:5](=[O:9])[CH:4]=1.[CH2:10](Br)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[CH2:10]([N:6]1[C:5](=[O:9])[CH:4]=[C:3]([NH:2][CH3:1])[N:8]=[CH:7]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 1354814476-(Methylamino)pyrimidin-4-ol2×

Product 1

HCID 598230553-Benzyl-6-(methylamino)pyrimidin-4(3H)-oneYield 43.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6-(Methylamino)pyrimidin-4(3H)-one (compound 1B) (3 g, 24 mmol, 1 eq), benzyl bromide (5.7 mL, 48 mmol, 2 eq) and potassium carbonate (6.96 g, 50.4 mmol, 2.1 eq) were stirred in ethanol (30 mL) at RT overnight. The solvent was removed in vacuo and the residue purified by silica chromatography to give 2.25 g of the title compound (43%). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.64 (d, J=4.29 Hz, 3 H) 4.92-5.01 (m, 2 H) 6.96 (q, J=4.63 Hz, 1 H) 7.22-7.30 (m, 3 H) 7.30-7.37 (m, 2 H) 8.24 (s, 1 H). [M+H] calc'd for C12H13N3O, 216; found, 216.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue purified by silica chromatography

Sources & evidence

ORD record
ord-9fe3e6fa53604e3c9f68e2746b6b1092
Source dataset
uspto-grants-2012_10
Patent number
US08293901B2

Reaction notes

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