Isopropanol → 5H,6H,7H,8H-pyrido(4,3-d)pyrimidine
Reaction equation
C([N:8]1[CH2:19][CH2:18][C:11]2[N:12]=[C:13](Cl)[N:14]=[C:15](Cl)[C:10]=2[CH2:9]1)C1C=CC=CC=1.Cl.Cl.C[C@H]1CN[C@H](C)CN1.CCN(C(C)C)C(C)C.CC(O)C>C(OCC)C>[N:12]1[C:11]2[CH2:18][CH2:19][NH:8][CH2:9][C:10]=2[CH:15]=[N:14][CH:13]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
A mixture of 6-benzyl-2,4-dichloro-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine (2.0 g, 6.80 mmol), (trans)-2,5-dimethylpiperazine dihydrochloride (7.63 g, 40.8 mmol), DIEA (15.4 mL, 88 mmol) and iPrOH (180 mL) was heated at 80° C. for 3.5 days. At that time the reaction was diluted with diethyl ether and the solid was removed by filtration. The filtrate was then washed with brine and the organic layer was dried (Na2SO4), filtered and concentrated to provide crude racemic 6-benzyl-2-chloro-4-(trans)-2,5-dimethylpiperazin-1-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine, which was then carried to the next step without further purification. MS (ESI+) m/z 372.2 (M+H)+
Workup
- customthe solid was removed by filtration
- washThe filtrate was then washed with brine
- dry with materialthe organic layer was dried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-4a7e994b8b1a4fb58a718ba0e2422692
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08846656B2
Reaction notes
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