Tetrahydropyrimidine-2-thione → 3-Benzyl-2,3,6,7-tetrahydro-2-phenyl-5H-thiazolo[3,2-a]pyrimidin-3-ol hydrobromide

HRID 1759377Notes

Reaction equation

HRID 1759377 reaction equation
[Br:1][CH:2]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:3](=[O:11])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[NH:18]1[CH2:23][CH2:22][CH2:21][NH:20][C:19]1=[S:24]>CC(C)=O>[BrH:1].[CH2:4]([C:3]1([OH:11])[N:20]2[CH2:21][CH2:22][CH2:23][N:18]=[C:19]2[S:24][CH:2]1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 2723785Tetrahydropyrimidine-2-thioneHCID 135503741-Bromo-1,3-diphenylpropan-2-one

Product 1

HCID 130389193-Benzyl-2,3,6,7-tetrahydro-2-phenyl-5H-thiazolo[3,2-a]pyrimidin-3-ol hydrobromideYield 56.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A solution of 2.9 grams of 1-bromo-1,3-diphenyl-2-propanone (Example 93) in 30 ml. of acetone is added to a solution of 1.16 grams of tetrahydro-2-pyrimidinethione in 100 ml. of acetone. A white precipitate forms in a few minutes. After standing at room temperature for four hours, the precipitate is collected, washed with acetone, and dried. Recrystallization from 20 ml. of ethanol yields 2.3 grams of the pure compound, melting at 192°-194° C. with decomposition.

Workup

  1. waitA white precipitate forms in a few minutes
  2. customthe precipitate is collected
  3. washwashed with acetone
  4. customdried
  5. customRecrystallization from 20 ml

Sources & evidence

ORD record
ord-f05937469f9a4dfdb642c37a4b49e297
Source dataset
uspto-grants-1982_07
Patent number
US04340734

Reaction notes

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