Cesium carbonate → 6-chloro-N-methyl-2-morpholino-N-(tetrahydro-2H-pyran-4-yl)pyrimidin-4-amine

HRID 1043806Notes

Reaction equation

[CH3:1][NH:2][CH:3]1[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1.C([O-])([O-])=O.[Cs+].[Cs+].Cl[C:16]1[CH:21]=[C:20]([Cl:22])[N:19]=[C:18]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[N:17]=1>CN1C(=O)CCC1>[Cl:22][C:20]1[N:19]=[C:18]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[N:17]=[C:16]([N:2]([CH3:1])[CH:3]2[CH2:8][CH2:7][O:6][CH2:5][CH2:4]2)[CH:21]=1

Participants

Conditions

Temperature: 95 °C

Procedure

The crude N-methyltetrahydro-2H-pyran-4-amine (104 mg, 0.9 mmol) was dissolved in NMP (0.8 mL). To the solution, Cs2CO3 (366 mg, 1.13 mmol) and 4-(4,6-dichloropyrimidin-2-yl)morpholine (prepared as in Method 22) (80 mg, 0.34 mmol) were added at room temperature. The reaction mixture was heated to 95° C. After 90 minutes, the reaction mixture was cooled to room temperature, filtered and purified by reverse phase preparative HPLC yielding 24 mg (23%) of pure 6-chloro-N-methyl-2-morpholino-N-(tetrahydro-2H-pyran-4-yl)pyrimidin-4-amine. LC/MS (m/z): 313.2 (MH+), Rt 2.61 minutes.

Workup

temperaturethe reaction mixture was cooled to room temperature
filtrationfiltered
custompurified by reverse phase preparative HPLC

Sources & evidence

ORD record: ord-3ab741ea9bc6460ba65b6e706204146f
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08563549B2

Reaction notes

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