Allyl bromide → HCID 14570168, compound

HRID 280699Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([CH2:9][C:10]2[CH:15]=[C:14]([O:16][CH3:17])[C:13]([O:18][CH3:19])=[C:12]([OH:20])[CH:11]=2)=[CH:4][N:3]=1.[CH2:21](Br)[CH:22]=[CH2:23]>>[CH2:21]([O:20][C:12]1[CH:11]=[C:10]([CH:15]=[C:14]([O:16][CH3:17])[C:13]=1[O:18][CH3:19])[CH2:9][C:5]1[C:6]([NH2:8])=[N:7][C:2]([NH2:1])=[N:3][CH:4]=1)[CH:22]=[CH2:23]

Participants

Reactant 2

HCID 7841Allyl bromide

HCID 128497693-Demethyltrimethoprim

Product 1

HCID 14570168HCID 14570168, compound

Procedure

The title compound was prepared from 2,4-diamino-5-(3-hydroxy-4,5-dimethoxybenzyl)pyrimidine (20.0 g, 72.4 mmol) and allyl bromide by the procedure of Example 1A. Recrystallization from 95% ethanol gave title compound as white crystals (14.9 g); mp 160°-162°. Anal. Calcd for C16H20N4O3 : C, 60.74; H, 6.37; N, 17.71. Found: C, 60.94; H, 6.45; N, 17.62.

Workup

customRecrystallization from 95% ethanol

Sources & evidence

ORD record: ord-d0121e1c77fc47da9e00f3827c29d37a
Source dataset: uspto-grants-1986_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04590271

Reaction notes

Loading…