Diethyl methylmalonate → 5-Hydroxy-3-(4-methoxybenzyl)-6,8-dimethylpyrido[2,3-d]pyrimidine-4,7(3H,8H)-dione

HRID 1260430Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([CH2:7][N:8]2[C:13](=[O:14])[CH:12]=[C:11]([NH:15][CH3:16])[N:10]=[CH:9]2)=[CH:5][CH:4]=1.[CH3:19][CH:20]([C:26]([O:28]CC)=O)[C:21]([O:23]CC)=O>C1(OC2C=CC=CC=2)C=CC=CC=1>[OH:28][C:26]1[C:12]2[C:13](=[O:14])[N:8]([CH2:7][C:6]3[CH:17]=[CH:18][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[CH:9]=[N:10][C:11]=2[N:15]([CH3:16])[C:21](=[O:23])[C:20]=1[CH3:19]

Participants

Conditions

Temperature: 240 °C

Procedure

3-(4-Methoxybenzyl)-6-(methylamino)pyrimidin-4(3H)-one (14.8 g, 60.2 mmol, 1 eq, compound 8A) and diethyl methylmalonate (61.6 mL, 361 mmol, 6 eq) were mixed in phenyl ether (25 mL) and heated at 240° C. for 2 days. The solution was allowed to RT and left standing overnight. The tan precipitate which formed was collected and washed with ether to give 15.2 g of the title compound as a tan solid (78%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.89 (s, 3H) 3.55 (s, 3H) 3.74 (s, 3H) 5.14 (s, 2H) 6.93 (d, J=8.59 Hz, 2H) 7.37 (d, J=8.59 Hz, 2H) 8.89 (s, 1H) 11.82 (s, 1H). %). [M+H] calc'd for C17H17N3O4, 328. found, 328.

Workup

customwas allowed to RT
waitleft
customThe tan precipitate which formed
customwas collected
washwashed with ether

Sources & evidence

ORD record: ord-3d6bee9b14424e9c943b54f3c0f6e0e0
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08470837B2

Reaction notes

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