Trifluoroacetic acid → Ethyl 3-hydroxy-4-oxo-9-phenyl-6,7-dihydro-4H-pyrido[1,2-a]pyrimidine-2-carboxylate

HRID 346489Notes

Reaction equation

C([O:8][C:9]1[C:14](=[O:15])[N:13]2[CH2:16][CH2:17][CH:18]=[C:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:12]2=[N:11][C:10]=1[C:26]([O:28][CH2:29][CH3:30])=[O:27])C1C=CC=CC=1.FC(F)(F)C(O)=O>ClCCl>[OH:8][C:9]1[C:14](=[O:15])[N:13]2[CH2:16][CH2:17][CH:18]=[C:19]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:12]2=[N:11][C:10]=1[C:26]([O:28][CH2:29][CH3:30])=[O:27]

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of intermediate 16, ethyl 3-(benzyloxy)-4-oxo-9-phenyl-6,7-dihydro-4H-pyrido[1,2-a]pyrimidine-2-carboxylate (0.320 g, 0.80 mmol) in dichloromethane (5 ml) was treated with trifluoroacetic acid (5 ml) and the resulting mixture was stirred at 25° C. for 16 h. The reaction mixture was then concentrated in vacuo and the residue was triturated with ether to give 0.189 g (76% yield) of the title material as a white solid; mp 151° C. 1HNMR 400 MHz (CDCl3) δ (ppm): 1.37 (3H, t, J=7.1 Hz, CH3), 2.67 (2H, m, CH2), 4.34 (2H, t, J=7.1 Hz, CH2), 4.37 (2H, q, J=7.1 Hz, OCH2), 6.70 (1H, t, J=4.8 Hz, CH), 7.38 (3H, m, aromatics), 7.55 (2H, m, aromatics), 10.70 (1H, s, OH). HRMS (ESI+) calculated for C17H17N2O4 [M+H+]: 313.1188; found: 313.1181.

Workup

concentrationThe reaction mixture was then concentrated in vacuo
customthe residue was triturated with ether

Sources & evidence

ORD record: ord-5213a36777f44806a5255463a55ce1c4
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07173022B2

Reaction notes

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