Ethyl 3-(triphenyl-lambda~5~-phosphanylidene)propanoate → HCID 86588095, compound

HRID 1828419Notes

Reaction equation

[CH:1]1([C:5]2[N:6]=[C:7]([CH2:10][CH2:11][C:12]3[CH:30]=[CH:29][N:15]4[C:16](=[O:28])[C:17]([CH:26]=O)=[C:18]([N:20]5[CH2:25][CH2:24][O:23][CH2:22][CH2:21]5)[N:19]=[C:14]4[CH:13]=3)[S:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[C:31]([CH2:36][CH:37]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:33][CH2:34][CH3:35])=[O:32]>C1(C)C=CC=CC=1>[CH:1]1([C:5]2[N:6]=[C:7]([CH2:10][CH2:11][C:12]3[CH:30]=[CH:29][N:15]4[C:16](=[O:28])[C:17](/[CH:26]=[C:36](\[CH3:37])/[C:31]([O:33][CH2:34][CH3:35])=[O:32])=[C:18]([N:20]5[CH2:25][CH2:24][O:23][CH2:22][CH2:21]5)[N:19]=[C:14]4[CH:13]=3)[S:8][CH:9]=2)[CH2:2][CH2:3][CH2:4]1

Participants

Conditions

Temperature: 130 °C

Procedure

8-[2-(4-Cyclobutyl-1,3-thiazol-2-yl)ethyl]-2-morpholino-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-carbaldehyde (100 mg, 0.236 mmol) dissolved in toluene (2 ml) was added with (carbethoxyethylidene)triphenylphosphorane (102 mg, 0.283 mmol) and refluxed by heating at 130° C. Then the regent was added until the reaction was completed, and 7 equivalents of the regent was finally added. After the reaction mixture was stirred for 4 days, the solvent was evaporated under reduced pressure, and the resulting residue was purified by thin layer silica gel chromatography (chloroform:methanol=40:1) to obtain 443 mg of yellow crystals in a mixture with triphenylphosphine oxide.

Workup

temperaturerefluxed
additionThen the regent was added until the reaction
addition7 equivalents of the regent was finally added
customthe solvent was evaporated under reduced pressure
customthe resulting residue was purified by thin layer silica gel chromatography (chloroform:methanol=40:1)

Sources & evidence

ORD record: ord-dbab635910e94aec8adad25e397795ef
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07056917B2

Reaction notes

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