Diisopropylethylamine → 8-[(E)-2-(4-Isopropyl-1,3-thiazol-2-yl)-1-ethenyl]-2-(tetrahydro-3-furanylmethoxy)-4H-pyrido[1,2-a]pyrimidin-4-one

HRID 1828508Notes

Reaction equation

[OH:1][C:2]1[N:3]=[C:4]2[CH:12]=[C:11](/[CH:13]=[CH:14]/[C:15]3[S:16][CH:17]=[C:18]([CH:20]([CH3:22])[CH3:21])[N:19]=3)[CH:10]=[CH:9][N:5]2[C:6](=[O:8])[CH:7]=1.C(N(C(C)C)CC)(C)C.I[CH2:33][CH:34]1[CH2:38][CH2:37][O:36][CH2:35]1>CN(C)C=O>[CH:20]([C:18]1[N:19]=[C:15](/[CH:14]=[CH:13]/[C:11]2[CH:10]=[CH:9][N:5]3[C:6](=[O:8])[CH:7]=[C:2]([O:1][CH2:33][CH:34]4[CH2:38][CH2:37][O:36][CH2:35]4)[N:3]=[C:4]3[CH:12]=2)[S:16][CH:17]=1)([CH3:22])[CH3:21]

Participants

Conditions

Temperature: 80 °C

Procedure

2-Hydroxy-8-[(E)-2-(4-isopropyl-1,3-thiazol-2-yl)-1-ethenyl]-4H-pyrido[1,2-a]-pyrimidin-4-one (210 mg, 0.670 mmol) was suspended in dimethylformamide (6.0 ml), added with diisopropylethylamine (600 μl) and 3-(iodomethyl)tetrahydrofuran (334 μl), and stirred overnight at 80° C. The reaction solution was further added with diisopropylethylamine (600 μl) and 3-(iodomethyl)tetrahydrofuran (334 μl) and stirred overnight at 80° C. The reaction mixture was concentrated, and the residue was purified by silica gel column chromatography (chloroform:methanol=100:0→100:1→100:2→100:5, v/v) to obtain the title compound (277 mg, quantitative).

Workup

stirringstirred overnight at 80° C
concentrationThe reaction mixture was concentrated
customthe residue was purified by silica gel column chromatography (chloroform

Sources & evidence

ORD record: ord-e5372b70f58849c493fadca2a077d97b
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07056917B2

Reaction notes

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