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

HRID 1642422Notes

Reaction equation

HRID 1642422 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.[CH2:20]([O:22][CH2:23][CH2:24][O:25][C:26]1[C:33]([O:34][CH3:35])=[CH:32][CH:31]=[CH:30][C:27]=1[CH:28]=O)[CH3:21].[O-]CC.[Na+]>>[CH2:20]([O:22][CH2:23][CH2:24][O:25][C:26]1[C:33]([O:34][CH3:35])=[CH:32][CH:31]=[CH:30][C:27]=1/[CH:28]=[CH: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:9]=[CH:10][C:11]([C:12]#[N:13])=[CH:14][CH:15]=1)[CH3:21]

Participants

4

Reactant 3

HCID 2723922Sodium ethoxideHCID 230098872-(2-Ethoxyethoxy)-3-methoxybenzaldehydeHCID 66752927HCID 66752927, compound

Product 1

HCID 444670074-{7-[(E)-2-(2-Ethoxyethoxy-3-methoxyphenyl]-1-ethenyl}-5-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidin-6-yl}benzonitrileYield 39%

Procedure

The title compound was prepared by condensation of Intermediate 4 (335 mg, 1.252 mmol) with 2-(2-ethoxyethoxy)-3-methoxy-benzaldehyde (339 mg, 1.753 mmol) in presence of sodium ethoxide (170 mg, 2.506 mmol) according to the procedure described in Example 9 to yield 231 mg of the desired product as a light yellow solid; 1H NMR (300 MHz, DMSO-d6) δ 1.16 (t, J=6.6 Hz, 3H), 3.45-3.52 (m, 4H), 3.78 (s, 3H), 4.00-4.08 (m, 2H), 6.78 (d, J=15.6 Hz, 1H), 6.94-7.01 (m, 3H), 7.50-7.58 (m, 3H), 7.92 (d, J=7.8 Hz, 2H), 8.02 (d, J=4.8 Hz, 1H), 8.20 (d, J=15.6 Hz, 1H); ESI-MS (m/z) 474.45 (M+H)+.

Sources & evidence

ORD record
ord-a0b2a26ef7634148894fefe7dfaebb81
Source dataset
uspto-grants-2012_02
Patent number
US08119647B2

Reaction notes

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