1,2-Dimethoxyethane → 7-Benzyl-2-chloro-4-phenyl-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine

HRID 2402525Notes

Reaction equation

[CH2:1]([N:8]1[CH2:17][CH2:16][C:15]2[C:14](Cl)=[N:13][C:12]([Cl:19])=[N:11][C:10]=2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:20]1(B(O)O)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(N(CC)CC)C.C(COC)OC>C(OCC)(=O)C.O>[CH2:1]([N:8]1[CH2:17][CH2:16][C:15]2[C:14]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[N:13][C:12]([Cl:19])=[N:11][C:10]=2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a round bottomed flask containing 7-benzyl-2,4-dichloro-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine (578 mg, 1.96 mmol) was added phenylboronic acid (260 mg, 2.13 mmol), dichloro-((bis-diphenylphosphino)ferrocenyl)-palladium (II) (complex with methylene chloride, 160 mg, 0.32 mmol), triethylamine (600 μL, 4.3 mmol), dimethoxyethane (20 mL), and water (0.5 mL). The reaction mixture was heated to 80° C. for 14 h, then cooled to rt and diluted with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate, dried over sodium sulfate, filtered, and concentrated on a rotary evaporator. The material was purified by flash column chromatography to afford 7-benzyl-2-chloro-4-phenyl-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine (210 mg, 32%).

Workup

temperaturecooled to rt
washThe organic layer was washed with saturated sodium bicarbonate
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated on a rotary evaporator
customThe material was purified by flash column chromatography

Sources & evidence

ORD record: ord-07656762633e4f5abbc80a5bdfd3d704
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08796294B2

Reaction notes

Loading…