Acetonitrile → 3,3-Dimethyl-1-{[6-(5-methyl-pyridin-2-yl)-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-4-ylamino]-methyl}-cyclohexanol
Reaction equation
Cl[C:2]1[C:3]2[CH2:11][N:10]([C:12]3[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][N:13]=3)[CH2:9][CH2:8][C:4]=2[N:5]=[CH:6][N:7]=1.[NH2:19][CH2:20][C:21]1([OH:29])[CH2:26][CH2:25][CH2:24][C:23]([CH3:28])([CH3:27])[CH2:22]1.C(#N)C.C(=O)(O)[O-].[Na+]>>[CH3:27][C:23]1([CH3:28])[CH2:24][CH2:25][CH2:26][C:21]([CH2:20][NH:19][C:2]2[C:3]3[CH2:11][N:10]([C:12]4[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][N:13]=4)[CH2:9][CH2:8][C:4]=3[N:5]=[CH:6][N:7]=2)([OH:29])[CH2:22]1Participants
5
Reactant 4
Product 1
Procedure
4-chloro-5,6,7,8-tetrahydro-6-(5-methylpyridin-2-yl)pyrido[4,3-d]pyrimidine (0.030 g, 0.00012 mol) and 1-aminomethyl-3,3-dimethyl-cyclohexanol (0.022 g, 0.00014 mol) in acetonitrile (3 mL, 0.06 mol) was heated via microwave in a sealed tube at at 180° C. for a total of 2 hours and five minutes. The reaction mixture was cooled to room temperature and poured into saturated sodium bicarbonate. The mixture was extracted with equal amounts of ethyl acetate and the organic layer was dried over magnesium sulfate. The residue was purified by flash chromatography over silica gel methanol/dichloromethane (0-10%) to yield the title compound.
Workup
- extractionThe mixture was extracted with equal amounts of ethyl acetate
- dry with materialthe organic layer was dried over magnesium sulfate
- customThe residue was purified by flash chromatography over silica gel methanol/dichloromethane (0-10%)
Sources & evidence
- ORD record
- ord-5a4f96fd9b2840b29bc65860decf3aba
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07745451B2
Reaction notes
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