Diisopropylethylamine → (R)-6-Benzyl-N-(1-(4-chlorophenyl)ethyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-amine
Reaction equation
[CH2:1]([N:8]1[CH2:18][CH2:17][C:11]2[N:12]=[CH:13][N:14]=[C:15](Cl)[C:10]=2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([C@H:26]([NH2:28])[CH3:27])=[CH:22][CH:21]=1.C(N(CC)C(C)C)(C)C>C(#N)C>[CH2:1]([N:8]1[CH2:18][CH2:17][C:11]2[N:12]=[CH:13][N:14]=[C:15]([NH:28][C@@H:26]([C:23]3[CH:24]=[CH:25][C:20]([Cl:19])=[CH:21][CH:22]=3)[CH3:27])[C:10]=2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 200 °C
Procedure
Two 20 mL microwave vials were charged with a half portion of 6-benzyl-4-chloro-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine (3.50 g, 13.5 mmol), (R)-1-(4-chloro-phenyl)-ethylamine (4.20 g, 27.0 mmol), N,N-diisopropylethylamine (4.7 mL, 27 mmol) and acetonitrile (20 mL); and the mixture was heated in a microwave at 200° C. for 2.5 h. The mixture was concentrated in vacuo, and the residue was taken up in CH2Cl2 (100 mL) and ethyl acetate (20 mL), washed with 0.5 M aq. NaH2PO4 (pH 4, 100 mL), dried (Na2SO4), and concentrated. The residue was purified on silica gel column (0-5% MeOH/CH2Cl2) to give a pale yellow foam (4.46 g).
Workup
- concentrationThe mixture was concentrated in vacuo
- washethyl acetate (20 mL), washed with 0.5 M aq. NaH2PO4 (pH 4, 100 mL)
- dry with materialdried (Na2SO4)
- concentrationconcentrated
- customThe residue was purified on silica gel column (0-5% MeOH/CH2Cl2)
Sources & evidence
- ORD record
- ord-d13081031d594769afcfc70f2213ad27
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08653091B2
Reaction notes
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