Sodium ethoxide → 7-[(E)-2-(2-Cyclopropylmethoxy-3-methoxyphenyl)-1-ethenyl]-6-(4-methoxy-phenyl)-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one

HRID 1642438Notes

Reaction equation

HRID 1642438 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:14](=[O:15])[N:13]3[CH:16]=[CH:17][S:18][C:12]3=[N:11][C:10]=2[CH3:19])=[CH:5][CH:4]=1.[CH:20]1([CH2:23][O:24][C:25]2[C:32]([O:33][CH3:34])=[CH:31][CH:30]=[CH:29][C:26]=2[CH:27]=O)[CH2:22][CH2:21]1.[O-]CC.[Na+]>C(O)C>[CH:20]1([CH2:23][O:24][C:25]2[C:32]([O:33][CH3:34])=[CH:31][CH:30]=[CH:29][C:26]=2/[CH:27]=[CH:19]/[C:10]2[N:11]=[C:12]3[S:18][CH:17]=[CH:16][N:13]3[C:14](=[O:15])[C:9]=2[C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[CH2:21][CH2:22]1

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 435604072-(Cyclopropylmethoxy)-3-methoxybenzaldehydeHCID 66752909HCID 66752909, compound

Product 1

HCID 444673867-[(E)-2-(2-Cyclopropylmethoxy-3-methoxyphenyl)-1-ethenyl]-6-(4-methoxy-phenyl)-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-oneYield 43.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The title compound was prepared by condensation of Intermediate 9 (350 mg, 1.283 mmol) with 2-cyclopropylmethoxy-3-methoxybenzaldehyde (371 mg, 1.799 mmol) in presence of sodium ethoxide (174 mg, 2.570 mmol) in ethanol (10 ml) according to the procedure of Example 24 afforded 255 mg of the desired product as a pale yellow solid; 1H NMR (300 MHz, DMSO-d6) δ 0.25-0.27 (m, 2H), 0.49-0.51 (m, 2H), 1.03-1.05 (m, 1H), 3.67-3.70 (m, 2H), 3.77-3.81 (m, 3H), 6.89-6.91 (m, 2H), 6.98-7.02 (m, 4H), 7.23-7.26 (m, 2H), 7.47-7.49 (m, 1H), 7.96-8.10 (m, 1H), 8.10-8.15 (m, 1H); ESI-MS (m/z) 461.39 (M+H)+.

Sources & evidence

ORD record
ord-ae29ce1f8097492084a8f85c7a6e5b30
Source dataset
uspto-grants-2012_02
Patent number
US08119647B2

Reaction notes

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