Chlorosulfonic acid → HCID 20572143, compound

HRID 1577299Notes

Reaction equation

HRID 1577299 reaction equation
[NH2:1][C:2]1[N+:7]([O-:8])=[C:6]([NH2:9])[CH:5]=[C:4]([N:10]2[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]2)[N:3]=1.Cl[S:18]([OH:21])(=[O:20])=[O:19].C(N(C(C)C)CC)(C)C>C(Cl)(Cl)Cl>[OH-:8].[NH2:1][C:2]1[N:3]=[C:4]([N:10]2[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]2)[CH:5]=[C:6]([NH2:9])[N+:7]=1[O:8][S:18]([OH:21])(=[O:20])=[O:19]

Participants

5

Reactant 3

HCID 24638Chlorosulfonic acidHCID 81531DiisopropylethylamineHCID 178480774HCID 178480774, compound

Product 1

HCID 20572143HCID 20572143, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 1.00 grams of 2,4-diamino-6-(4-methyl-1-piperazinyl)pyrimidine-3-oxide, 1.50 grams of chlorosulfonic acid, and 2.5 grams of di-isopropylethylamine in 25 ml of chloroform is stirred overnight. The mixture is concentrated in vacuo. The residue is stirred with aqueous sodium bicarbonate, filtered and washed with ether to give the crude product. This is recrystallized from DMF and ethyl acetate to yield the purified 2,6-diamino-4-(4-methyl-1-piperazinyl)-1-(sulfooxy)pyrimidinium hydroxide, inner salt.

Workup

  1. concentrationThe mixture is concentrated in vacuo
  2. stirringThe residue is stirred with aqueous sodium bicarbonate
  3. filtrationfiltered
  4. washwashed with ether
  5. customto give the crude product
  6. customThis is recrystallized from DMF and ethyl acetate

Sources & evidence

ORD record
ord-7f89ea10ddfb47998fc5e4c0886acc3b
Source dataset
uspto-grants-1981_09
Patent number
US04287338

Reaction notes

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