Benzaldehyde → 7-{(E)-2-[2-(2,2-Dimethylpropoxy)-3-methoxyphenyl]vinyl}-5H-[1,3]thiazolo-[3,2-a]pyrimidin-5-one

HRID 1642383Notes

Reaction equation

HRID 1642383 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[CH:8][C:7]=2/[CH:14]=[CH:15]/[C:16]2[N:17]=[C:18]3[S:26][CH:25]=[CH:24][N:19]3[C:20](=[O:23])[C:21]=2I)[CH2:3][CH2:2]1.[CH:27](=O)C1C=CC=CC=1.[H-].[Na+]>CS(C)=O>[CH3:2][C:1]([CH3:3])([CH3:27])[CH2:4][O:5][C:6]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[CH:8][C:7]=1/[CH:14]=[CH:15]/[C:16]1[N:17]=[C:18]2[S:26][CH:25]=[CH:24][N:19]2[C:20](=[O:23])[CH:21]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 24758Sodium hydrideHCID 66753592HCID 66753592, compound2×

Product 1

HCID 667532687-{(E)-2-[2-(2,2-Dimethylpropoxy)-3-methoxyphenyl]vinyl}-5H-[1,3]thiazolo-[3,2-a]pyrimidin-5-oneYield 177%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

This compound was prepared using Step 2 intermediate from Intermediate 2 (1.00 g, 2.160 mmol), [2-(2,2-dimethylpropoxy)-3-methoxy)]benzaldehyde (527 mg, 2.316 mmol) and NaH (92 mg, 2.685 mmol) in dry DMSO (10 ml) according to the procedure outlined in Intermediate 2, Step 3 to yield a crude residue which was purified by column chromatography using 2% ethyl acetate in chloroform to afford the 1.416 g of the desired compound as a white solid: 1H NMR (300 MHz, DMSO-d6) 1.08 (s, 9H), 3.56 (s, 2H), 3.79 (s, 3H), 6.26 (s, 1H), 7.01-7.17 (m, 2H), 7.33-7.35 (m, 1H), 7.46 (d, J=4.8 Hz, 1H), 7.97 (d, J=4.8 Hz, 1H), 8.11-8.16 (m, 1H); ESI-MS (m/z) 371.52 (M+H)+.

Workup

  1. customThis compound was prepared
  2. customto yield a crude residue which
  3. customwas purified by column chromatography

Sources & evidence

ORD record
ord-dc896a3ea8a846889c55087346ce16fb
Source dataset
uspto-grants-2012_02
Patent number
US08119647B2

Reaction notes

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