3-Pentanol → HCID 86606453, compound
Reaction equation
[CH3:1][CH2:2][CH:3]([OH:6])[CH2:4][CH3:5].N1([C:12](N2C=CN=C2)=[O:13])C=CN=C1.CCN(C(C)C)C(C)C.Cl.[Cl:29][C:30]1[C:35]([O:36][CH3:37])=[C:34]([O:38][CH:39]2[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]2)[N:33]=[CH:32][N:31]=1>C1COCC1>[CH2:2]([CH:3]([O:6][C:12]([N:42]1[CH2:43][CH2:44][CH:39]([O:38][C:34]2[C:35]([O:36][CH3:37])=[C:30]([Cl:29])[N:31]=[CH:32][N:33]=2)[CH2:40][CH2:41]1)=[O:13])[CH2:4][CH3:5])[CH3:1]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
Pentan-3-ol (0.88 g, 9.99 mmol) and di-imidazol-1-yl-methanone (1.39, 8.57 mmol) were added to THF (10 mL) and stirred at 50° C. for one hour. DIPEA (1.38 g, 10.7 mmol) and 4-chloro-5-methoxy-6-(piperidin-4-yloxy)-pyrimidine HCl (2.00 g, 7.14 mmol) were added, the vessel sealed and heated by microwave at 150° C. for one hour. Upon cooling the reaction mixture was partitioned between water and Ethyl Acetate, the organic phase washed with brine and dried with Sodium Sulfate. The crude material was purified by column chromatograph (silica gel) with 10-30% EtOAc/Hexanes to yield 1.0 grams (39%) of the desired product, as a white solid. 1HNMR (CDCl3, 400 MHz) δ 0.91 (t, J=7.83 Hz, 6H), 1.55-1.63 (m, 4H), 1.78-1.88 (m, 2H), 1.99-2.08 (m, 2H), 3.39-3.46 (m, 2H), 3.78-3.85 (m, 2H), 3.92 (s, 3H), 4.67 (m, 1H), 5.36-5.43 (m, 1H), 8.26 (s, 1H). Exact mass calculated for C16H24ClN3O4: 357.15. found: 358.3 (MH+).
Workup
- customthe vessel sealed
- temperatureheated by microwave at 150° C. for one hour
- temperatureUpon cooling the reaction mixture
- customwas partitioned between water and Ethyl Acetate
- washthe organic phase washed with brine
- dry with materialdried with Sodium Sulfate
- customThe crude material was purified by column chromatograph (silica gel) with 10-30% EtOAc/Hexanes
Sources & evidence
- ORD record
- ord-7aa55d639b724b52ad9778f5f1a71388
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08362248B2
Reaction notes
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