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

HRID 1642433Notes

Reaction equation

HRID 1642433 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[S:21][CH:20]=[CH:19][N:5]2[C:6](=[O:18])[C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=1.[CH:22]1([CH2:25][O:26][C:27]2[CH:28]=[C:29]([CH:32]=[CH:33][C:34]=2[O:35][CH3:36])[CH:30]=O)[CH2:24][CH2:23]1.[O-]CC.[Na+]>C(O)C>[CH:22]1([CH2:25][O:26][C:27]2[CH:28]=[C:29](/[CH:30]=[CH:1]/[C:2]3[N:3]=[C:4]4[S:21][CH:20]=[CH:19][N:5]4[C:6](=[O:18])[C:7]=3[C:8]3[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:15])[F:16])=[CH:10][CH:9]=3)[CH:32]=[CH:33][C:34]=2[O:35][CH3:36])[CH2:23][CH2:24]1

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 222466233-(Cyclopropylmethoxy)-4-methoxybenzaldehydeHCID 667528027-Methyl-6-[4-(trifluoromethyl)phenyl]-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one

Product 1

HCID 444673137-[(E)-2-(3-Cyclopropylmethoxy-4-methoxyphenyl)-1-ethenyl]-6-[4-(trifluoro methyl)-phenyl]-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-oneYield 42.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The title compound was synthesized by condensation of Intermediate 5 (400 mg, 1.350 mmol) with 3-cyclopropylmethoxy-4-methoxybenzaldehyde (417 mg, 2.025 mmol) in presence of sodium ethoxide (183 mg, 2.701 mmol) in ethanol (20 ml) according to the procedure described in Example 24 to give 289 mg of the desired product as an off-white solid; 1H NMR (300 MHz, DMSO-d6) δ 0.23-0.30 (m, 2H), 0.50-0.58 (m, 2H), 1.12-1.18 (m, 1H), 3.72-3.80 (m, 5H), 6.60 (d, J=15.6 Hz, 1H) 6.94-7.00 (m, 3H), 7.48-7.53 (m, 1H), 7.58-7.64 (m, 2H), 7.78-7.84 (m, 3H), 7.98-8.05 (m, 1H); ESI-MS (m/z) 499.12 (M+H)+.

Sources & evidence

ORD record
ord-0b9641c3daa8443a8412f916017d74fc
Source dataset
uspto-grants-2012_02
Patent number
US08119647B2

Reaction notes

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