N-bromobutanimide → Ethyl 5-bromo-2-cyclopropyl-1,6-dihydro-6-oxo-4-pyrimidinecarboxylate

HRID 249649Notes

Reaction equation

HRID 249649 reaction equation
[CH:1]1([C:4]2[NH:5][C:6]([CH:11]([O:15][CH2:16][CH3:17])[O:12]CC)=[CH:7][C:8](=[O:10])[N:9]=2)[CH2:3][CH2:2]1.[Br:18]N1C(=O)CCC1=O>ClCCl>[Br:18][C:7]1[C:8](=[O:10])[NH:9][C:4]([CH:1]2[CH2:3][CH2:2]2)=[N:5][C:6]=1[C:11]([O:15][CH2:16][CH3:17])=[O:12]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 178471100HCID 178471100, compound

Product 1

HCID 136342271Ethyl 5-bromo-2-cyclopropyl-1,6-dihydro-6-oxo-4-pyrimidinecarboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-cyclopropyl-6-(diethoxymethyl)-4(1H)-pyrimidinone (i.e. the title product of Step A) (2.9 g, 12.1 mmol) in dichloromethane (75 mL) was added N-bromosuccinimide (4.76 g, 26.8 mmol). The reaction mixture was stirred overnight. The solvent was removed with a rotary evaporator. The residue was purified by MPLC (1→4% methanol in dichloromethane as eluant) to afford the title compound as a white solid (2.68 g).

Sources & evidence

ORD record
ord-8265653390ae41fc9519cf3970ba4a73
Source dataset
uspto-grants-2011_01
Patent number
US07863220B2

Reaction notes

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