Morpholine → (R)-Tert-butyl 3-(6-methoxy-2-morpholinopyrimidin-4-ylamino)piperidine-1-carboxylate

HRID 1507488Notes

Reaction equation

[CH3:1][O:2][C:3]1[N:8]=[C:7](S(C)(=O)=O)[N:6]=[C:5]([NH:13][C@@H:14]2[CH2:19][CH2:18][CH2:17][N:16]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:15]2)[CH:4]=1.[NH:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1>C(#N)C>[CH3:1][O:2][C:3]1[N:8]=[C:7]([N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)[N:6]=[C:5]([NH:13][C@@H:14]2[CH2:19][CH2:18][CH2:17][N:16]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:15]2)[CH:4]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Compound 19 (150 mg, 0.405 mmol) was dissolved in acetonitrile (2 mL) and morpholine (0.282 mL, 3.24 mmol) was added, The solution was sealed and heated to 100° C. for 18 h. The solution was concentrated and the residue was purified by column chromatography on silica gel, eluting with EtOAc/hexane to give the title compound as a colorless oil. 1H NMR (CDCl3) δ 5.13 (s, 1H), 4.52-4.51 (m, 1H), 3.82 (s, 3H), 3.72 (s, 8H), 3.62-3.59 (m, 2H), 3.14-3.10 (m, 2H), 1.94 (m, 1H), 1.72-1.70 (m, 1H), 1.55-1.53 (m, 2H), 1.43 (s, 9H); LCMS 2.02 min, 394 (M+H).

Workup

customThe solution was sealed
concentrationThe solution was concentrated
customthe residue was purified by column chromatography on silica gel
washeluting with EtOAc/hexane

Sources & evidence

ORD record: ord-6e7fae773d4b40079e5fbfa7bb1c43fa
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221809B2

Reaction notes

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