N-bromobutanimide → 2-Bromo-1-(2-cyclopropylmethoxypyrimidin-5-yl)ethanone

HRID 633733Notes

Reaction equation

[CH:1]1([CH2:4][O:5][C:6]2[N:11]=[CH:10][C:9]([C:12]([O:14]CC)=[CH2:13])=[CH:8][N:7]=2)[CH2:3][CH2:2]1.[Br:17]N1C(=O)CCC1=O>C1COCC1.O.C(OCC)(=O)C>[Br:17][CH2:14][C:12]([C:9]1[CH:8]=[N:7][C:6]([O:5][CH2:4][CH:1]2[CH2:3][CH2:2]2)=[N:11][CH:10]=1)=[O:13]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 480 mg (2.18 mmol) of 2-cyclopropylmethoxy-5-(1-ethoxyvinyl)pyrimidine in 8 mL of a THF/H2O mixture: (6/2: v/v) is cooled to 0° C. under argon. After addition of 380.02 mg (2.11 mmol) of N-bromosuccinimide, the reaction mixture is maintained at 0° C. for 1 hour. The solution obtained is taken up in ethyl acetate and washed with aqueous NaHCO3 solution and then with saturated NaCl solution. The organic phase is dried over magnesium sulfate and evaporated to dryness. The residue is purified by chromatography on silica gel (eluent: 80/20 DCM/MeOH) to give 410 mg of 2-bromo-1-(2-cyclopropylmethoxypyrimidin-5-yl)ethanone, the characteristics of which are as follows:

Workup

customThe solution obtained
washwashed with aqueous NaHCO3 solution
dry with materialThe organic phase is dried over magnesium sulfate
customevaporated to dryness
customThe residue is purified by chromatography on silica gel (eluent: 80/20 DCM/MeOH)

Sources & evidence

ORD record: ord-9372a79e407c4764adbbc7f5b1a76598
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321790B2

Reaction notes

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