Cesium carbonate → 6-(4-Cyclopropylmethoxyphenyl)-7-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one

HRID 1642390Notes

Reaction equation

[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:15](=[O:16])[N:14]3[CH:17]=[CH:18][S:19][C:13]3=[N:12][C:11]=2[CH3:20])=[CH:6][CH:5]=1)[CH3:2].[CH:21]1(CBr)C[CH2:22]1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.C(OCC)(=O)C>[CH:2]1([CH2:1][O:3][C:4]2[CH:5]=[CH:6][C:7]([C:10]3[C:15](=[O:16])[N:14]4[CH:17]=[CH:18][S:19][C:13]4=[N:12][C:11]=3[CH3:20])=[CH:8][CH:9]=2)[CH2:22][CH2:21]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of Step 1 intermediate from Intermediate 10 (500 mg, 1.932 mmol) in DMF (5 ml) was added cyclopropylmethyl bromide (0.313 g, 2.321 mmol) at room temperature followed by Cs2CO3 (1.88 g, 5.770 mmol) and the reaction temperature was heated to 80° C. for 15.0 h overnight. The reaction mixture was diluted with ethyl acetate, washed with water and brine and purified by column chromatography using 1% methanol in chloroform to afford the desired compound; 1H NMR (300 MHz, CDCl3) δ 0.35-0.37 (m, 2H), 0.59-0.61 (m, 2H), 1.01-1.03 (m, 1H), 2.19 (s, 3H), 3.80-3.85 (m, 2H), 7.09-7.11 (m, 2H), 7.26-7.29 (m, 2H), 7.52 (d, J=4.8 Hz, 1H), 7.97 (d, J=4.5 Hz, 1H); MS (m/z) 313.25 (M+H)+.

Workup

washwashed with water and brine
custompurified by column chromatography

Sources & evidence

ORD record: ord-5e70c4664af04b52b1ad18f9c8c9a581
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08119647B2

Reaction notes

Loading…