Hydrochloric Acid → 4-Methyl-5-(2-methyl-pyrimidin-4-yl)-thiazol-2-ylamine

HRID 1430117Notes

Reaction equation

C[Si](Cl)(C)C.[CH3:6][C:7]1[N:8]=[C:9]([NH:19]C(=O)C)[S:10][C:11]=1[C:12]1[CH:17]=[CH:16][N:15]=[C:14]([CH3:18])[N:13]=1.Cl>C(O)C>[CH3:6][C:7]1[N:8]=[C:9]([NH2:19])[S:10][C:11]=1[C:12]1[CH:17]=[CH:16][N:15]=[C:14]([CH3:18])[N:13]=1

Participants

Conditions

Temperature: 50 °C

Procedure

Trimethylsilylchloride (0.3 ml) is added at room temperature to a suspension of N-[4-methyl-5-(2-methyl-pyrimidin-4-yl)-thiazol-2-yl]-acetamide (29 mg, prepared as described in WO 04/096797) in ethanol (2 ml) at room temperature. The mixture is heated at 50° C. for 18 hours, conc. HCl (0.2 ml) is added and the heating at 50° C. is continued for a further 46 hours. Following cooing the mixture is partitioned between saturated aqueous NaHCO3 and CH2Cl2 containing 10% methanol and extracted a further 2×CH2Cl2. Evaporation of the organic layers gives the title compound as a beige solid. 1H nmr (d4-methanol, 400 MHz) 8.44 (d, J=7 hz, 1H), 7.33 (d, J=7 Hz, 1H), 2.58 (s, 3H), 2.51 (s, 3H).

Workup

customis partitioned between saturated aqueous NaHCO3 and CH2Cl2 containing 10% methanol
extractionextracted a further 2×CH2Cl2
customEvaporation of the organic layers

Sources & evidence

ORD record: ord-889aa6a2a7504cf9a3936e423f53975a
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08940771B2

Reaction notes

Loading…