HCID 59854662, compound → HCID 59854727, compound

HRID 2112770Notes

Reaction equation

HRID 2112770 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-9a74ed5ae3404f7eb699ca33f68a0f16
Source dataset
uspto-grants-2009_04
Patent number
US07524853B2

Reaction notes

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