3-Chloro-1-butyne → 2,4-Diamino-5-[3,4-dimethoxy-5-(1-methyl-2-propynyloxy)benzyl]pyrimidine

HRID 280013

Reaction equation

HRID 280013 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.Cl[CH:22]([CH3:25])[C:23]#[CH:24]>>[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([CH2:9][C:10]2[CH:11]=[C:12]([O:20][CH:23]([CH3:24])[C:22]#[CH:25])[C:13]([O:18][CH3:19])=[C:14]([O:16][CH3:17])[CH:15]=2)=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 304433-Chloro-1-butyneHCID 128497693-Demethyltrimethoprim

Product 1

HCID 128498022,4-Diamino-5-[3,4-dimethoxy-5-(1-methyl-2-propynyloxy)benzyl]pyrimidineYield 62%

Procedure

The title compound was prepared in 62% yield from 2,4-diamino-5-(3-hydroxy-4,5-dimethoxybenzyl)pyrimidine and 3-chloro-1-butyne by the procedure of Example 1A. Crystallization from methanol gave white solid; mp 153°-155°. Anal. Calcd for C17H20N4O3 : C, 62.18; H, 6.14; N, 17.06. Found: C, 61.93; H, 6.22; N, 16.98.

Workup

  1. customCrystallization from methanol
  2. customgave white solid

Sources & evidence

ORD record
ord-1f4067bd24644e1ea1473f23c7fb53bd
Source dataset
uspto-grants-1986_05
Patent number
US04587342

Linked notes

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