Thiomorpholine → 2-Imino-6-methyl-4-(thiomorpholin-4-yl)pyrimidin-1(2H)-ol

HRID 1282910Notes

Reaction equation

HRID 1282910 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH3:8])[N:5]([OH:9])[C:4](=[NH:10])[N:3]=1.[NH:11]1[CH2:16][CH2:15][S:14][CH2:13][CH2:12]1>CS(C)=O>[NH:10]=[C:4]1[N:3]=[C:2]([N:11]2[CH2:16][CH2:15][S:14][CH2:13][CH2:12]2)[CH:7]=[C:6]([CH3:8])[N:5]1[OH:9]

Participants

4

Reactant 2

HCID 67164ThiomorpholineHCID 133718454-Chloro-2-imino-6-methylpyrimidin-1(2H)-ol

Product 1

HCID 190856242-Imino-6-methyl-4-(thiomorpholin-4-yl)pyrimidin-1(2H)-olYield 50.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 32 g of 4-chloro-1,2-dihydro-2-imino-6-methyl-1-pyrimidinol, 46 g of thiomorphline, and 200 ml of dimethyl sulfoxide was heated at 100°C in a nitrogen atmosphere for 17 hours. The solvent is removed under high vacuum. The residue is shaken with 5% ammonium hydroxide solution and with chloroform. The chloroform layer is washed with water, dried over sodium sulfate and the solvent removed. Trituration of the residue with ether gives 23 g of a solid mp 208°-210°C. Recrystallization from acetone-methanol gives a white crystalline solid, mp 243°-245°C.

Workup

  1. customThe solvent is removed under high vacuum
  2. washThe chloroform layer is washed with water
  3. dry with materialdried over sodium sulfate
  4. customthe solvent removed

Sources & evidence

ORD record
ord-07ab393ebbd34da6b73847397be6577a
Source dataset
uspto-grants-1976_08
Patent number
US03973016

Reaction notes

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