Benzylamine → 3-benzyl-2-isobutylpyrido[3,4-d]pyrimidin-4(3H)-one

HRID 1867458Notes

Reaction equation

[CH2:1]([C:5]1O[C:7](=[O:15])[C:8]2[CH:14]=[CH:13][N:12]=[CH:11][C:9]=2[N:10]=1)[CH:2]([CH3:4])[CH3:3].[CH2:16]([NH2:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[OH-].[Na+]>C(Cl)(Cl)Cl>[CH2:16]([N:23]1[C:7](=[O:15])[C:8]2[CH:14]=[CH:13][N:12]=[CH:11][C:9]=2[N:10]=[C:5]1[CH2:1][CH:2]([CH3:3])[CH3:4])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 2-isobutyl-4H-pyrido[3,4-d][1,3]oxazin-4-one (3.0 g, 14.68 mmol) in CHCl3 was added benzylamine (1.73 g, 16.15 mmol) and the reaction was heated to 60° C. After 3 h, the reaction was cooled to room temperature and solvent removed in vacuo. The resulting residue was dissolved in ethylene glycol and sodium hydroxide (0.385 g, 9.62 mmol) was added. The reaction was stirred overnight at 140° C. After cooling to room temperature and extracting with DCM, the organic solution was washed with water. The solution was dried over sodium sulfate and filtered. Concentration of the organic solution provided the title compound as a brown oil. 1H NMR (500 MHz, CDCl3) δ 1.01 (d, J=7 Hz, 6H), 2.33-2.38 (m, 1H), 2.68 (d, J=7 Hz, 2H), 5.43 (s, 2H), 7.16 (d, J=7.5 Hz, 2H), 7.30-7.40 (m, 3H), 8.06 (d, J=5 Hz, 1H), 8.68 (d, J=5 Hz, 1H), 9.13 (s, 1H). MS [M+H] C18H19N3O=294.1.

Workup

temperaturethe reaction was cooled to room temperature
customsolvent removed in vacuo
dissolutionThe resulting residue was dissolved in ethylene glycol
temperatureAfter cooling to room temperature
extractionextracting with DCM
washthe organic solution was washed with water
dry with materialThe solution was dried over sodium sulfate
filtrationfiltered

Sources & evidence

ORD record: ord-77c210080410451194b517963a707512
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07632839B2

Reaction notes

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