Acetic Acid → 5,6,7,8-Tetrahydro-7-(phenylmethyl)pyrido(3,4-d)pyrimidin-4(3H)-one

HRID 885052Notes

Reaction equation

C[O-].[Na+].C(O)(=O)C.[CH:8]([NH2:10])=[NH:9].Cl.[CH2:12]([N:19]1[CH2:24][CH2:23][CH:22]([C:25](OCC)=[O:26])[C:21](=O)[CH2:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(O)(=O)C>CO.O>[CH2:12]([N:19]1[CH2:24][CH2:23][C:22]2[C:25](=[O:26])[NH:10][CH:8]=[N:9][C:21]=2[CH2:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 25 °C

Procedure

Part A: To a solution of sodium methoxide (25 wgt-% in methanol) (67.6 mL, 296 mmol) and methanol (70 mL) at 25° C. was added formamidine acetate (11.00 g, 106 mmol) and then ethyl N-benzyl-3-oxo-4-piperidine carboxylate hydrochloride (25.16 g, 84 mmol). The resulting mixture was stirred at 25° C. for 20 h. The mixture was cooled to 0° C. Water (90 mL) was added, followed by the dropwise addition of acetic acid (6.05 mL, 106 mmol), and the reaction mixture was stirred at 25° C. for another 3 h. The mixture was reduced in volume under vacuum until most of the methanol had been removed. The suspension was filtered. The solids were washed with water and then dried under vacuum to afford 7-benzyl-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4(3H)-one (16.10 g, 79%) as an off-white solid; Mass Spec.: m/e: 242.06 (M+H)+ [calc'd: 242.12]; 1H NMR (500 MHz, CDCl3) δ 12.61 (br s, 1H), 7.99 (s, 1H), 7.38-7.26 (m, 5H), 3.73 (m, 2H), 3.50 (m, 2H), 2.74 (m, 2H), 2.66 (m, 2H).

Workup

temperatureThe mixture was cooled to 0° C
stirringthe reaction mixture was stirred at 25° C. for another 3 h
customhad been removed
filtrationThe suspension was filtered
washThe solids were washed with water
customdried under vacuum

Sources & evidence

ORD record: ord-1c91fde9273e467a8fcdb9e08149f883
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08242124B2

Reaction notes

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