1,1-Diethylguanidine → 5-(2-(Diethylamino)pyrimidin-4-yl)-4-methylthiazol-2-amine

HRID 444888Notes

Reaction equation

HRID 444888 reaction equation
[OH-].[Na+].CN(C)[CH:5]=[CH:6][C:7]([C:9]1[S:13][C:12]([N:14]=CN(C)C)=[N:11][C:10]=1[CH3:19])=O.[CH2:21]([N:23]([CH2:27][CH3:28])[C:24]([NH2:26])=[NH:25])[CH3:22]>COCCO>[NH2:14][C:12]1[S:13][C:9]([C:7]2[CH:6]=[CH:5][N:26]=[C:24]([N:23]([CH2:27][CH3:28])[CH2:21][CH3:22])[N:25]=2)=[C:10]([CH3:19])[N:11]=1

Participants

5

Reactant 3

HCID 144671,1-DiethylguanidineHCID 14798Sodium HydroxideHCID 67218485N'-[5-(3-dimethylamino-acryloyl)-4-methyl-thiazol-2-yl]-N,N-dimethyl-formamidine

Product 1

HCID 574170815-(2-(Diethylamino)pyrimidin-4-yl)-4-methylthiazol-2-amine

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Conditions

Temperature
125 °C

Procedure

Powdered sodium hydroxide (150 mg) is added to a solution of N′-[5-(3-dimethylamino-acryloyl)-4-methyl-thiazol-2-yl]-N,N-dimethyl-formamidine (0.5 g, prepared as described by S. Wang et al J. Med. Chem. 2004, 47, 1662-1675.) and 1,1-diethylguanidine (259 mg) in 2-methoxyethanol (1.9 ml) and the mixture heated at 125° C. for 1 hour with stirring. The reaction mixture is concentrated under vacuum and purified by normal phase chromatography, eluent; DCM/EtOAc, to give the title compound. ESI-MS: M+H 264 and M−H 262.

Workup

  1. concentrationThe reaction mixture is concentrated under vacuum
  2. custompurified by normal phase chromatography, eluent

Sources & evidence

ORD record
ord-51f6cb5899f14fb0ba89e462729ee49d
Source dataset
uspto-grants-2013_07
Patent number
US08476268B2

Reaction notes

Loading…