1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 66760455, compound

HRID 1188710Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[CH:10]([NH:12][C:13]1[C:18](/[CH:19]=[CH:20]/[C:21](OCC)=[O:22])=[CH:17][N:16]=[C:15]([S:26][CH3:27])[N:14]=1)[CH2:9][CH2:8]2.N12CCCN=C1CCCCC2>CN1CCCC1=O.C(OCC)(=O)C.[Cl-].[Na+].O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[CH:10]([N:12]1[C:13]3[N:14]=[C:15]([S:26][CH3:27])[N:16]=[CH:17][C:18]=3[CH:19]=[CH:20][C:21]1=[O:22])[CH2:9][CH2:8]2

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of (E)-ethyl 3-(4-(7-methoxy-2,3-dihydro-1H-inden-1-ylamino)-2-(methylthio)pyrimidin-5-yl)acrylate (0.30 g, 0.78 mmol) in N-methylpyrrolidinone (1.8 mL) was added 1,8-diazabicyclo[5.4.0]undec-7-ene (0.35 mL, 0.35 g, 2.29 mmol) and the reaction was stirred for 4 h at 120° C. The reaction mixture was poured onto ice water and diluted with ethyl acetate (8 mL) and saturated brine solution (2.5 mL). The two phases were separated, and the organic layer was washed with 1 M hydrochloric acid (1×7 mL), water (1×7 mL), dried over sodium sulfate, filtered and evaporated to 8-(7-methoxy-2,3-dihydro-1H-inden-1-yl)-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one as a brown oil (0.40 g, 1.18 mmol, quant.). ESMS m/z 340 (M+H)+.

Workup

additionThe reaction mixture was poured onto ice water
customThe two phases were separated
washthe organic layer was washed with 1 M hydrochloric acid (1×7 mL), water (1×7 mL)
dry with materialdried over sodium sulfate
filtrationfiltered
customevaporated to 8-(7-methoxy-2,3-dihydro-1H-inden-1-yl)-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one as a brown oil (0.40 g, 1.18 mmol, quant.)

Sources & evidence

ORD record: ord-52dd33d39834420082dcddf5749ee957
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08674095B2

Reaction notes

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