Water → 4-Methyl-5-(2-(1-methylcyclopropyl)-pyrimidin-4-yl)thiazol-2-amine

HRID 2370388Notes

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:23]1([C:26]([NH2:28])=[NH:27])[CH2:25][CH2:24]1.O>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]([C:23]2([CH3:22])[CH2:25][CH2:24]2)[N:27]=1

Participants

Conditions

Temperature: 125 °C

Procedure

Powdered sodium hydroxide (5.86 g) is added to a solution of N′-[5-(3-dimethylamino-acryloyl)-4-methyl-thiazol-2-yl]-N,N-dimethyl-formamidine (13 g, prepared as described by S. Wang et al J. Med. Chem. 2004, 47, 1662-1675.) and 1-methyl-cyclopropanecarboxamidine hydrochloride (7.2 g, prepared as described in EP0227415) in 2-methoxyethanol (98 ml) and the mixture heated at 125° C. for 1 hour with stirring. The reaction mixture is cooled, water is added, and the title compound isolated by filtration. ESI-MS: M+H 247 and M−H 245.

Workup

temperatureThe reaction mixture is cooled

Sources & evidence

ORD record: ord-f1bf89152e9048feb3190bc89d4a3380
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08710085B2

Reaction notes

Loading…