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

HRID 1642443Notes

Reaction equation

HRID 1642443 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[S:22][CH:21]=[CH:20][N:5]2[C:6](=[O:19])[C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]([F:18])([F:17])[F:16])=[CH:10][CH:9]=1.[CH2:23]([O:28][C:29]1[C:36]([O:37][CH3:38])=[CH:35][CH:34]=[CH:33][C:30]=1[CH:31]=O)[CH2:24][CH:25]([CH3:27])[CH3:26].[O-]CC.[Na+]>C(O)C>[CH2:23]([O:28][C:29]1[C:36]([O:37][CH3:38])=[CH:35][CH:34]=[CH:33][C:30]=1/[CH:31]=[CH:1]/[C:2]1[N:3]=[C:4]2[S:22][CH:21]=[CH:20][N:5]2[C:6](=[O:19])[C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]([F:17])([F:18])[F:16])=[CH:10][CH:9]=1)[CH2:24][CH:25]([CH3:27])[CH3:26]

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 43471291HCID 43471291, compoundHCID 66753265HCID 66753265, compound

Product 1

HCID 444675317-[(E)-2-{2-Isopentyloxy-3-methoxyphenyl}-1-ethenyl]-6-[4-(trifluoro methoxy)phenyl]-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-oneYield 49.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The title compound was prepared by condensation of Intermediate 15 (350 mg, 1.071 mmol) with 2-isopentyloxy-3-methoxybenzaldehyde (334 mg, 1.501 mmol) in the presence of sodium ethoxide (146 mg, 2.147 mmol) in ethanol (15 ml) according to the procedure outlined in Example 24 to afford 280 mg of the desired product as a light yellow solid; 1H NMR (300 MHz, DMSO-d6) δ 0.93 (d, J=6.3 Hz, 6H), 1.45 (q, J=6.6 Hz, 2H), 1.85-1.91 (m, 1H), 3.77 (s, 3H), 3.86 (t, J=6.6 Hz, 2H), 6.86-6.94 (m, 2H), 7.00-7.06 (m, 2H), 7.46-7.51 (m, 5H), 7.99 (d, J=4.8 Hz, 1H), 8.07 (d, J=15.6 Hz, 1H); ESI-MS (m/z) 531.20 (M+H)+.

Sources & evidence

ORD record
ord-423da71ff4ed477b947c8d0e9b219516
Source dataset
uspto-grants-2012_02
Patent number
US08119647B2

Reaction notes

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