Sodium ethoxide → 4-{7-[(E)-2-(3-Methoxy-2-neopentyloxyphenyl)-1-ethenyl]-5-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidin-6-yl}benzonitrile

HRID 1642420Notes

Reaction equation

HRID 1642420 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[S:19][CH:18]=[CH:17][N:5]2[C:6](=[O:16])[C:7]=1[C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=1.[CH3:20][O:21][C:22]1[C:23]([O:30][CH2:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[C:24]([CH:27]=[CH:28][CH:29]=1)[CH:25]=O.[O-]CC.[Na+]>C(O)C>[CH3:20][O:21][C:22]1[C:23]([O:30][CH2:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[C:24](/[CH:25]=[CH:1]/[C:2]2[N:3]=[C:4]3[S:19][CH:18]=[CH:17][N:5]3[C:6](=[O:16])[C:7]=2[C:8]2[CH:9]=[CH:10][C:11]([C:12]#[N:13])=[CH:14][CH:15]=2)[CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 66752927HCID 66752927, compoundHCID 866360773-Methoxy-2-neopentyloxybenzaldehyde

Product 1

HCID 444680804-{7-[(E)-2-(3-Methoxy-2-neopentyloxyphenyl)-1-ethenyl]-5-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidin-6-yl}benzonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The title compound was prepared from Intermediate 4 (400 mg, 1.496 mmol), 3-methoxy-2-neopentyloxybenzaldehyde (465 mg, 2.094 mmol) and sodium ethoxide (203 mg, 2.992 mmol) in ethanol (25 ml) according to the procedure described in Example 9 to give 290 mg of the product as a light yellow solid; 1H NMR (300 MHz, DMSO-d6) δ 1.03 (s, 9H), 3.53 (s, 2H), 3.77 (s, 3H), 6.77 (d, J=15.6 Hz, 1H), 6.99 (br s, 3H), 7.51-7.57 (m, 3H), 7.91-7.99 (m, 3H), 8.26 (d, J=15.0 Hz, 1H); ESI-MS (m/z) 472.26 (M+H)+.

Sources & evidence

ORD record
ord-8b40ad5ae9ba49bf9f7fff72e7722857
Source dataset
uspto-grants-2012_02
Patent number
US08119647B2

Reaction notes

Loading…