HCID 59198381, compound → HCID 66820106, compound
Reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[CH:5]=[C:4]([O:14][CH:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[N:3]=1.[CH3:21][O:22][C:23]1[C:28](B2OC(C)(C)C(C)(C)O2)=[CH:27][N:26]=[C:25]([NH2:38])[N:24]=1>>[CH3:21][O:22][C:23]1[C:28]([C:2]2[N:7]=[C:6]([N:8]3[CH2:13][CH2:12][O:11][CH2:10][CH2:9]3)[CH:5]=[C:4]([O:14][CH:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)[N:3]=2)=[CH:27][N:26]=[C:25]([NH2:38])[N:24]=1Participants
Procedure
According to Example 1 the reaction of 2-chloro-4-morpholino-6-(tetrahydro-2H-pyran-4-yloxy)pyrimidine (20 mg, 0.067 mmol) with 4-methoxy-5-(4,4,5,5-tetramethyl(1,3,2-dioxaborolan-2-yl))pyrimidine-2-ylamine (50 mg, 0.200 mmol) afforded 4′-methoxy-4-morpholino-6-(tetrahydro-2H-pyran-4-yloxy)-2,5′-bipyrimidin-2′-amine. The crude product was treated with morpholine (0.058 mL, 0.667 mmol) in NMP (2 mL) and heated under microwave irradiation (high absorption, fixed hold time) for 60 minutes at 200° C. Additional morpholine (0.058 mL, 0.667 mmol) was added and the solution heated at 200° C. under microwave irradiation for another 30 minutes, then another 60 minutes at 210° C. Upon cooling the material was directly purified by reverse-phase HPLC. After lyophilization, the TFA salt of 2-amino-5-(4-morpholino-6-(tetrahydro-2H-pyran-4-yloxy)pyrimidin-2-yl)pyrimidin-4(3H)-one was isolated as an off white solid (17.1 mg, 68%), LCMS (m/z): 375.1 (MH+). Rt: 1.74 min.
Sources & evidence
- ORD record
- ord-1d255c6516864641b0e322ffe7f48587
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08173647B2
Reaction notes
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