6-Benzyl-2,4-dichloro-5,6,7,8-tetrahydropyrido(4,3-d)pyrimidine → (R)-6-Benzyl-2-chloro-4-(4-methoxy-3,3-dimethylpiperidin-1-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine

HRID 80837Notes

Reaction equation

[CH2:1]([N:8]1[CH2:19][CH2:18][C:11]2[N:12]=[C:13]([Cl:17])[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-].[CH3:21][O:22][C@@H:23]1[CH2:28][CH2:27][NH2+:26][CH2:25][C:24]1([CH3:30])[CH3:29]>CC(O)C>[CH2:1]([N:8]1[CH2:19][CH2:18][C:11]2[N:12]=[C:13]([Cl:17])[N:14]=[C:15]([N:26]3[CH2:27][CH2:28][C@@H:23]([O:22][CH3:21])[C:24]([CH3:30])([CH3:29])[CH2:25]3)[C:10]=2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 6-benzyl-2,4-dichloro-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine (5.55 g, 18.8 mmol) in iPrOH (170 mL) was added (R)-4-methoxy-3,3-dimethylpiperidin-1-ium chloride, Example 7-D (3.08 g, 17.1 mmol) and TEA (7.2 mL, 51.4 mmol). The reaction mixture was then heated overnight at 50° C. At that point the solvent was removed in vacuo and the residue was purified via FCC (0-50% EtOAc/heptane) to give the title compound. MS (ESI+) m/z 401.3 (M+H)+.

Workup

customAt that point the solvent was removed in vacuo
customthe residue was purified via FCC (0-50% EtOAc/heptane)

Sources & evidence

ORD record: ord-6a47e8d797a949c5b603b8b9287eb325
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846656B2

Reaction notes

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