Sodium Hydroxide → 4-Methyl-5-(2-(2-methylcyclopropyl)-pyrimidin-4-yl)thiazol-2-amine

HRID 2370389Notes

Reaction equation

HRID 2370389 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.Cl.[CH3:22][C@@H:23]1[CH2:25][C@H:24]1[C:26]([NH2:28])=[NH:27]>COCCO>[CH3:19][C:10]1[N:11]=[C:12]([NH2:14])[S:13][C:9]=1[C:7]1[CH:6]=[CH:5][N:28]=[C:26]([CH:24]2[CH2:25][CH:23]2[CH3:22])[N:27]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 67218485N'-[5-(3-dimethylamino-acryloyl)-4-methyl-thiazol-2-yl]-N,N-dimethyl-formamidineHCID 86641155rac-(1R,2R)-2-methylcyclopropane-1-carboximidamide hydrochloride

Product 1

HCID 592937074-Methyl-5-(2-(2-methylcyclopropyl)-pyrimidin-4-yl)thiazol-2-amine

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Conditions

Temperature
125 °C

Procedure

Powdered sodium hydroxide (300 mg) is added to a solution of N′-[5-(3-dimethylamino-acryloyl)-4-methyl-thiazol-2-yl]-N,N-dimethyl-formamidine (1 g, prepared as described by S. Wang et al J. Med. Chem. 2004, 47, 1662-1675.) and cis/trans 2-methyl-cyclopropanecarboxamidine hydrochloride (0.61 g, prepared as described in WO 03/087064) in 2-methoxyethanol (3.8 ml) and the mixture heated at 125° C. for 1 hour with stirring. The reaction mixture is cooled, filtered, washing with water to give the title compound. MS: M+H 247 and M−H 245.

Workup

  1. temperatureThe reaction mixture is cooled
  2. filtrationfiltered
  3. washwashing with water

Sources & evidence

ORD record
ord-fea14cc640014fb0b64304a136791f61
Source dataset
uspto-grants-2014_04
Patent number
US08710085B2

Reaction notes

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