Acetyl bromide → HCID 21303242, compound

HRID 2194807Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:15]([CH2:16][CH3:17])=[C:14]([O:18]C)[N:13]=[C:12]([O:20]C)[N:11]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1.[C:22](Br)(=[O:24])[CH3:23]>>[CH3:8][C:6]1[CH:5]=[C:4]([N:9]([C:10]2[NH:11][C:12](=[O:20])[NH:13][C:14](=[O:18])[C:15]=2[CH2:16][CH3:17])[C:22](=[O:24])[CH3:23])[CH:3]=[C:2]([CH3:1])[CH:7]=1

Participants

Reactant 2

HCID 10482Acetyl bromide

HCID 67050513HCID 67050513, compound

Product 1

HCID 21303242HCID 21303242, compoundYield 86%

Procedure

(3,5-Dimethyl-phenyl)-(5-ethyl-2,6-dimethoxy-pyrimidin-4-yl)-amine (5 g, 17.4 mmol) was refluxed with acetyl bromide (50 mL) for 18 hr. After cooling to room temperature, the mixture was evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent, ethyl acetate:hexane (2:1)) to afford 4.5 g (86%) of a white solid. m.p. 238-239° C.; 1H-NMR (200 MHz, CDCl3) δ 0.93 (3H, t, J=7.5 Hz), 2.05-2.15 (3H, m), 2.24-2.40 (8H, m), 6.94-6.99 (3H, m); m/z (EI) 301(M+).

Workup

customthe mixture was evaporated in vacuo
customthe residue was purified by silica gel column chromatography (eluent, ethyl acetate:hexane (2:1))

Sources & evidence

ORD record: ord-d60337e2551143278c5d262690326593
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08334295B2

Reaction notes

Loading…