Ethanol → 2-(methylsulfanyl)-6-(3,5-dimethoxyphenyl)-8-ethyl-8H-pyrido[2,3-d]pyrimidin-7-one

HRID 2184178Notes

Reaction equation

[CH2:1]([NH:3][C:4]1[C:9]([CH:10]=O)=[CH:8][N:7]=[C:6]([S:12][CH3:13])[N:5]=1)[CH3:2].C(O[C:17](=[O:29])[CH2:18][C:19]1[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[C:21]([O:27][CH3:28])[CH:20]=1)C.N12CCCN=C1CCCCC2.C(O)C>CS(C)=O>[CH3:13][S:12][C:6]1[N:7]=[CH:8][C:9]2[CH:10]=[C:18]([C:19]3[CH:20]=[C:21]([O:27][CH3:28])[CH:22]=[C:23]([O:25][CH3:26])[CH:24]=3)[C:17](=[O:29])[N:3]([CH2:1][CH3:2])[C:4]=2[N:5]=1

Participants

Conditions

Temperature: 47.5 °C

Procedure

4.8 Kg of 4-ethylamino-2-methylsulfanyl-pyrimidine-5-carboxaldehyde and 5.5 Kg of (3,5-dimethoxyphenyl)-acetic acid ethyl ester were dissolved in 10 L of DMSO at room temperature and stirred. 4.4 Kg of 1,8-diazabicyclo[5.4.0]undec-7-ene was added to the reaction mixture. The mixture was heated at about 45-50° C. for at least 3 hours. The reaction was monitored by reverse-phase HPLC. When the reaction was completed, ethyl alcohol (3 L) was added to the reaction vessel, which was cooled to 5-15° C. The yellow product was precipitated and collected by filtration, washed with a mixture of isopropyl alcohol and water (3 L+3 L), and dried in a vacuum tray dryer at about 40-45° C. for at least 12 hours using a house vacuum (˜30 in Hg) to provide 7.3 Kg (84% yield) of 2-(methylsulfanyl)-6-(3,5-dimethoxyphenyl)-8-ethyl-8H-pyrido[2,3-d]pyrimidine-7-one. Proton NMR is consistent with the structure.

Workup

temperaturewas cooled to 5-15° C
customThe yellow product was precipitated
filtrationcollected by filtration
washwashed with a mixture of isopropyl alcohol and water (3 L+3 L)
customdried in a vacuum tray dryer at about 40-45° C. for at least 12 hours

Sources & evidence

ORD record: ord-32d4e353e6d940548e3acefe26fecfb6
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06900316B2

Reaction notes

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