Water → (S)-tert-butyl 2-(4-(5-chloro-2-isopropoxypyrimidin-4-ylamino)phenyl)morpholine-4-carboxylate

HRID 710273Notes

Reaction equation

[CH3:1][C:2](C)([O-:4])[CH3:3].[K+].Cl[C:8]1[N:13]=[C:12]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([C@@H:21]3[O:26][CH2:25][CH2:24][N:23]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:22]3)=[CH:17][CH:16]=2)[C:11]([Cl:34])=[CH:10][N:9]=1.O>CC(O)C>[Cl:34][C:11]1[C:12]([NH:14][C:15]2[CH:16]=[CH:17][C:18]([C@@H:21]3[O:26][CH2:25][CH2:24][N:23]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:22]3)=[CH:19][CH:20]=2)=[N:13][C:8]([O:4][CH:2]([CH3:3])[CH3:1])=[N:9][CH:10]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a stirred solution of potassium tert.-butoxide (116 mg, 1.03 mmol) in propan-2-ol (2 mL) was added (S)-tert-butyl 2-(4-(2,5-dichloropyrimidin-4-ylamino)phenyl)morpholine-4-carboxylate (110 mg, 0.26 mmol) and the mixture was shaken at 90° C. overnight. After cooling, the reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was dried over MgSO4 and evaporated. The residue was purified by column chromatography (silica gel, 5 to 15% ethyl acetate in heptan, 10 g ISCO column). White foam (58 mg, 50%). MS (ISP): 449.3 ([{35Cl}M+H]+), 451.1 ([{37Cl}M+H]+).

Workup

temperatureAfter cooling
extractionextracted with ethyl acetate
dry with materialThe organic layer was dried over MgSO4
customevaporated
customThe residue was purified by column chromatography (silica gel, 5 to 15% ethyl acetate in heptan, 10 g ISCO column)

Sources & evidence

ORD record: ord-053089de4d374f38b955fbe296a049f5
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181230B2

Reaction notes

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