Sodium hydride → 7-[(E)-2-(2-Isobutoxy-3-methoxyphenyl)vinyl]-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one

HRID 1642381Notes

Reaction equation

HRID 1642381 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.[H-].[Na+]>CS(C)=O>[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)[CH:1]([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 66753592HCID 66753592, compound2×

Product 1

HCID 667527727-[(E)-2-(2-Isobutoxy-3-methoxyphenyl)vinyl]-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-oneYield 64.9%

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-isobutoxy-3-methoxy)benzaldehyde (494 mg, 2.376 mmol) and NaH (95 mg, 3.958 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 DCM to afford the 500 mg of the desired compound as a white solid: 1H NMR (300 MHz, DMSO-d6) 1.05 (d, J=6.9 Hz, 6H), 2.01-2.06 (m, 1H), 3.69 (d, J=6.3 Hz, 2H), 3.80 (s, 3H), 6.28 (s, 1H), 6.94-7.18 (m, 3H), 7.34 (d, J=6.3 Hz, 1H), 7.47 (d, J=5.1 Hz, 1H), 7.97 (d, J=4.8 Hz, 1H), 8.09 (d, J=16.2 Hz, 1H).

Workup

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

Sources & evidence

ORD record
ord-4bdd4c69ee8d4bda9e335e9216c216b6
Source dataset
uspto-grants-2012_02
Patent number
US08119647B2

Reaction notes

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