Dimethylformamide → 4,6-Dihydroxy-2-(4-methoxybenzylsulfanyl)pyrimidine

HRID 2276288

Reaction equation

HRID 2276288 reaction equation
CN(C=O)C.[OH:6][C:7]1[CH:12]=[C:11]([OH:13])[N:10]=[C:9]([SH:14])[N:8]=1.C(N(CC)CC)C.[CH3:22][O:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28]Cl)=[CH:26][CH:25]=1>O>[OH:6][C:7]1[CH:12]=[C:11]([OH:13])[N:10]=[C:9]([S:14][CH2:28][C:27]2[CH:30]=[CH:31][C:24]([O:23][CH3:22])=[CH:25][CH:26]=2)[N:8]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 699934-Methyloxybenzyl chlorideHCID 178516656HCID 178516656, compound

Product 1

HCID 1784917094,6-Dihydroxy-2-(4-methoxybenzylsulfanyl)pyrimidineYield 82.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A DMF (500 ml) solution of 4,6-dihydroxy-2-mercaptopyrimidine (50 g, 346 mmol), triethylamine (62.7 ml, 450 mmol), 4-methoxybenzyl chloride (52.8 ml, 381 mmol) was heated and stirred at 100° C. for 1 hour 45 minutes. The reaction solution was poured into water and stirred for a while, and the precipitated crystals were collected by filtration and air-dried to obtain 75.2 g (82% yield) of 4,6-dihydroxy-2-(4-methoxybenzylsulfanyl)pyrimidine.

Workup

  1. stirringstirred for a while
  2. filtrationthe precipitated crystals were collected by filtration
  3. customair-dried

Sources & evidence

ORD record
ord-e98b9b70765a4320b7a2163bd1a14c57
Source dataset
uspto-grants-2015_09
Patent number
US09132130B2

Linked notes

Loading…