HCID 59854662, compound → HCID 59854727, compound

HRID 2375345Notes

Reaction equation

HRID 2375345 reaction equation
[CH2:1]([N:8]1[C:13](=[O:14])[C:12]2[C:15]3[CH2:21][CH2:20][CH2:19][CH2:18][C:16]=3[S:17][C:11]=2[N:10]=[C:9]1[C:22]1[CH:27]=[C:26]([O:28][CH3:29])[C:25]([O:30][CH3:31])=[C:24]([O:32][CH3:33])[CH:23]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=C[NH+]=CC=1.[O-:40][Cr](Cl)(=O)=O>ClCCl>[CH2:1]([N:8]1[C:13](=[O:14])[C:12]2[C:15]3[CH2:21][CH2:20][CH2:19][C:18](=[O:40])[C:16]=3[S:17][C:11]=2[N:10]=[C:9]1[C:22]1[CH:23]=[C:24]([O:32][CH3:33])[C:25]([O:30][CH3:31])=[C:26]([O:28][CH3:29])[CH:27]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 59854662HCID 59854662, compoundHCID 178418287HCID 178418287, compound2×

Product 1

HCID 59854727HCID 59854727, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-Benzyl-2-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydro-3H-benzo[4,5]thieno[2,3-d]pyrimidin-4-one (Compound No.1) (8.2 g, 17.7 mmol) dissolved in dry dichloromethane (30 ml) was added quickly to a mixture of PCC (19.2 g, 89.0 mmol, 500 mol-%) in dichloromethane (200 ml). During refluxing PCC was added several times until the reaction was completed. The reaction mixture was filtered through Celite with dichloromethane. The crude product was purified by flash chromatography. The yield of the compound No. 2 was 4.1 g (48%).

Workup

  1. additionwas added several times until the reaction
  2. filtrationThe reaction mixture was filtered through Celite with dichloromethane
  3. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-cfbf0d2b78994dceb2c2f92e8ae12293
Source dataset
uspto-grants-2008_12
Patent number
US07465739B2

Reaction notes

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