2-Methoxyethanol → 5-(2-(2,6-Dichlorobenzyl)pyrimidin-4-yl)-4-methylthiazol-2-amine

HRID 1430116Notes

Reaction equation

HRID 1430116 reaction equation
CN(C)/[CH:3]=[CH:4]/[C:5]([C:7]1[S:11][C:10]([N:12]=CN(C)C)=[N:9][C:8]=1[CH3:17])=O.[Cl:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[C:21]=1[CH2:27][C:28]([NH2:30])=[NH:29].COCCO.[OH-].[Na+]>O>[Cl:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[C:21]=1[CH2:27][C:28]1[N:30]=[C:5]([C:7]2[S:11][C:10]([NH2:12])=[N:9][C:8]=2[CH3:17])[CH:4]=[CH:3][N:29]=1

Participants

6

Reactant 4

HCID 80192-MethoxyethanolHCID 14798Sodium HydroxideHCID 5973572,6-DichlorophenylacetamidineHCID 67218484N'-[5-((E)-3-dimethylamino-acryloyl)-4-methyl-thiazol-2-yl]-N,N-dimethylformamidine

Product 1

HCID 575066535-(2-(2,6-Dichlorobenzyl)pyrimidin-4-yl)-4-methylthiazol-2-amine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of N′-[5-((E)-3-dimethylamino-acryloyl)-4-methyl-thiazol-2-yl]-N,N-dimethyl-formamidine (1 g), 2,6-dichlorophenylacetamidine (0.90 g) and 2-methoxyethanol (3.8 ml) is stirred at room temperature for 30 minutes. NaOH (0.3 g) is added and the mixture stirred at 125° C. for 1 hr. After cooling to room temperature water is added and the mixture evaporated to dryness and then purified by normal phase chromatography on silica gel eluting with a gradient from CH2Cl2 to EtOAc to give the title compound as a beige solid.

Workup

  1. stirringthe mixture stirred at 125° C. for 1 hr
  2. additionis added
  3. customthe mixture evaporated to dryness
  4. custompurified by normal phase chromatography on silica gel eluting with a gradient from CH2Cl2 to EtOAc

Sources & evidence

ORD record
ord-87aa7ac5cf504dbd8a5229bb442c9d08
Source dataset
uspto-grants-2015_01
Patent number
US08940771B2

Reaction notes

Loading…