(4-Methoxy-benzyl)-[4-methyl-5-(2-morpholin-4-yl-pyrimidin-4-yl)-thiazol-2-yl]-amine → 4-Methyl-5-(2-morpholin-4-yl-pyrimidin-4-yl)-thiazol-2-ylamine

HRID 1951192Notes

Reaction equation

COC1C=CC(C[NH:8][C:9]2[S:10][C:11]([C:15]3[CH:20]=[CH:19][N:18]=[C:17]([N:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)[N:16]=3)=[C:12]([CH3:14])[N:13]=2)=CC=1>FC(F)(F)C(O)=O.O>[CH3:14][C:12]1[N:13]=[C:9]([NH2:8])[S:10][C:11]=1[C:15]1[CH:20]=[CH:19][N:18]=[C:17]([N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[N:16]=1

Participants

Conditions

Temperature: 75 °C

Procedure

A solution comprising (4-methoxy-benzyl)-[4-methyl-5-(2-morpholin-4-yl-pyrimidin-4-yl)-thiazol-2-yl]-amine (25c) (0.45 g, 1.13 mmol) in trifluoroacetic acid:water (95:5) (10 ml) is heated at 75° C. for days. The solvent is removed in vacuo and the crude residue is dissolved in ethyl acetate. The pH is adjusted to pH12 using 2N sodium hydroxide and the layers are separated. The aqueous layer is extracted with ethyl acetate (2×30 ml). The organic portions are combined and washed with brine (50 ml), dried over MgSO4 and concentrated in vacuo to yield the titled compound as a brown solid.

Workup

customThe solvent is removed in vacuo
dissolutionthe crude residue is dissolved in ethyl acetate
customthe layers are separated
extractionThe aqueous layer is extracted with ethyl acetate (2×30 ml)
washwashed with brine (50 ml)
dry with materialdried over MgSO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-8c7f8a191e05474a866482fb25528157
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08404684B2

Reaction notes

Loading…