1,8-Diazabicyclo(5.4.0)undec-7-ene → (R)-2-amino-4-methyl-8-(tetrahydrofuran-3-yl)pyrido[2,3-d]pyrimidin-7(8H)-one

HRID 422001Notes

Reaction equation

C1CCN2C(=NCCC2)CC1.[NH2:12][C:13]1[N:18]=[C:17]([CH3:19])[C:16](/[CH:20]=[CH:21]/[C:22](OCC)=[O:23])=[C:15]([NH:27][C@@H:28]2[CH2:32][CH2:31][O:30][CH2:29]2)[N:14]=1>O>[NH2:12][C:13]1[N:18]=[C:17]([CH3:19])[C:16]2[CH:20]=[CH:21][C:22](=[O:23])[N:27]([C@@H:28]3[CH2:32][CH2:31][O:30][CH2:29]3)[C:15]=2[N:14]=1

Participants

Conditions

Temperature: 170 °C

Procedure

To a flask were added DBU (20 mL) and (R,E)-ethyl 3-(2-amino-4-methyl-6-(tetrahydrofuran-3-ylamino)pyrimidin-5-yl)acrylate (3.9 g, 13.4 mmol). The reaction mixture was stirred at 170° C. for 24 h under nitrogen. The mixture was allowed to cool to room temperature and was diluted with water. The aqueous layer was extracted with ethyl acetate (100 mL×3). The combined organic layers were washed with brine, separated and dried with MgSO4. The mixture was purified by chromatography to give (R)-2-amino-4-methyl-8-(tetrahydrofuran-3-yl)pyrido[2,3-d]pyrimidin-7(8H)-one (1.59 g, 48% yield); MS (EI) for C12H14N4O2: 247.1 (MH+).

Workup

temperatureto cool to room temperature
extractionThe aqueous layer was extracted with ethyl acetate (100 mL×3)
washThe combined organic layers were washed with brine
customseparated
dry with materialdried with MgSO4
customThe mixture was purified by chromatography

Sources & evidence

ORD record: ord-9ee4746647eb4e5794cc1200867c2706
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08101622B2

Reaction notes

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