1,1-Diphenylacetone → 3-Diphenylmethyl-2,3,6,7-tetrahydro-6,6-dimethyl-5H-thiazolo[3,2-a]pyrimidin-3-ol hydrobromide

HRID 1759374

Reaction equation

HRID 1759374 reaction equation
[C:1]1([CH:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8](=[O:10])[CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:17]CC(=O)C(C1C=CC=CC=1)C1C=CC=CC=1.[CH3:34][C:35]1([CH3:42])[CH2:40][NH:39][C:38](=[S:41])[NH:37][CH2:36]1>CC(C)=O>[BrH:17].[C:11]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8]2([OH:10])[N:39]3[CH2:40][C:35]([CH3:42])([CH3:34])[CH2:36][N:37]=[C:38]3[S:41][CH2:9]2)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 699071,1-DiphenylacetoneHCID 27946353-Bromo-1,1-diphenylacetone2×HCID 38664875,5-Dimethyl-1,4,5,6-tetrahydro-pyrimidine-2-thiol

Product 1

HCID 155712123-Diphenylmethyl-2,3,6,7-tetrahydro-6,6-dimethyl-5H-thiazolo[3,2-a]pyrimidin-3-ol hydrobromide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A 2.1 g. portion of 1,1-diphenyl-2-propanone is converted to 1-bromo-3,3-diphenyl-2-propanone as described in Example 22. This 1-bromo-3,3-diphenyl-2-propanone is dissolved in 15 ml. of acetone and added to a boiling mixture of 1.0 g. of tetrahydro-5,5-dimethyl-2(1H)-pyrimidinethione in 50 ml. of acetone. The mixture is allowed to stand at room temperature for 24 hours and the resulting solid is collected by filtration, giving the desired product, m.p. 259°-261° C.

Workup

  1. filtrationthe resulting solid is collected by filtration

Sources & evidence

ORD record
ord-74b9700bce794469a10ff051d82ec604
Source dataset
uspto-grants-1982_07
Patent number
US04340734

Linked notes

Loading…