Dimethylformamide → tert-Butyl (E)-3-{2-hydroxy-8-[(4-isopropyl-1,3-thiazol-2-yl)methoxy]-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl}-2-propenoate

HRID 1828432Notes

Reaction equation

[OH:1][C:2]1[N:3]=[C:4]2[CH:14]=[C:13]([O:15][CH2:16][C:17]3[S:18][CH:19]=[C:20]([CH:22]([CH3:24])[CH3:23])[N:21]=3)[CH:12]=[CH:11][N:5]2[C:6](=[O:10])[C:7]=1[CH:8]=O.CN(C)C=O.[C:30]([O:34][C:35]([CH:37]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:36])([CH3:33])([CH3:32])[CH3:31]>O1CCCC1>[OH:1][C:2]1[N:3]=[C:4]2[CH:14]=[C:13]([O:15][CH2:16][C:17]3[S:18][CH:19]=[C:20]([CH:22]([CH3:24])[CH3:23])[N:21]=3)[CH:12]=[CH:11][N:5]2[C:6](=[O:10])[C:7]=1/[CH:8]=[CH:37]/[C:35]([O:34][C:30]([CH3:31])([CH3:32])[CH3:33])=[O:36]

Participants

Conditions

Temperature: 100 °C

Procedure

2-Hydroxy-8-[(4-isopropyl-1,3-thiazol-2-yl)methoxy]-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-carbaldehyde (45 mg, 0.13 mmol) dissolved in tetrahydrofuran (2 ml) and dimethylformamide (1 ml) was added with (tert-butoxycarbonylmethylene)triphenyl-phosphorane (60 mg, 0.16 mmol) and refluxed by heating at 100° C. for 2 hours. The reaction solution was returned to room temperature and concentrated under reduced pressure, and the residue was purified by thin layer silica gel chromatography (chloroform:methanol=20:1) to obtain 36 mg (62%) of the title compound.

Workup

temperaturerefluxed
customwas returned to room temperature
concentrationconcentrated under reduced pressure
customthe residue was purified by thin layer silica gel chromatography (chloroform:methanol=20:1)

Sources & evidence

ORD record: ord-3bcf1357faca44ca90a8bfecd44121cc
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07056917B2

Reaction notes

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