Phenol → HCID 59854780, compound

HRID 2375347Notes

Reaction equation

HRID 2375347 reaction equation
[CH2:1]([N:8]1[C:13](=[O:14])[C:12]2[C:15]3[CH2:21][CH2:20][C:19]([CH:22]=[O:23])=[C:18](Cl)[C:16]=3[S:17][C:11]=2[N:10]=[C:9]1[C:25]1[CH:30]=[C:29]([O:31][CH3:32])[C:28]([O:33][CH3:34])=[C:27]([O:35][CH3:36])[CH:26]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:37]1([OH:43])[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.[OH-].[K+]>CCCC[N+](CCCC)(CCCC)CCCC.[Br-]>[CH2:1]([N:8]1[C:13](=[O:14])[C:12]2[C:15]3[CH2:21][CH2:20][C:19]([CH:22]=[O:23])=[C:18]([O:43][C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)[C:16]=3[S:17][C:11]=2[N:10]=[C:9]1[C:25]1[CH:30]=[C:29]([O:31][CH3:32])[C:28]([O:33][CH3:34])=[C:27]([O:35][CH3:36])[CH:26]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 14797Potassium HydroxideHCID 59854770HCID 59854770, compound

Product 1

HCID 59854780HCID 59854780, compound

Reagents, catalysts & solvents 1

HCID 74236Tetrabutylammonium BromideCatalyst

Procedure

3-Benzyl-8-chloro-4-oxo-2-(3,4,5-trimethoxyphenyl)-3,4,5,6-tetrahydro-benzo[4,5]thieno[2,3-d]pyrimidine-7-carbaldehyde (Compound No. 3) (50 mg, 96 μmol), phenol (13.5 mg, 143.4 μmol), KOH powder (8.0 mg, 143.4 μmol) and TBAB (1.0 mg) were heated at 85° C. for five hours and at 60° C. for 4,5 hours. The reaction mixture was filtered through cotton wool and evaporated. The crude product was purified by flash-chromatography. The compound No. 5 was isolated as a by-product.

Workup

  1. filtrationThe reaction mixture was filtered through cotton wool
  2. customevaporated
  3. customThe crude product was purified by flash-chromatography
  4. custom5 was isolated as a by-product

Sources & evidence

ORD record
ord-aeacb91f0ee54bc3b6ebe7036fc8842d
Source dataset
uspto-grants-2008_12
Patent number
US07465739B2

Reaction notes

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