Acryloyl chloride → HCID 69746631, compound

HRID 2181348Notes

Reaction equation

HRID 2181348 reaction equation
[C:1](Cl)(=[O:4])[CH:2]=[CH2:3].[CH3:6][N:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1.Br[C:14]1[C:22]2[C:21](=[O:23])[N:20]([CH3:24])[C:19](=[O:25])[N:18]([CH2:26][CH:27]([CH3:29])[CH3:28])[C:17]=2[S:16][C:15]=1[CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[C:37]([F:40])([F:39])[F:38].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(N(CC)CC)C>[CH3:24][N:20]1[C:21](=[O:23])[C:22]2[C:14]([CH:3]=[CH:2][C:1]([N:10]3[CH2:11][CH2:12][N:7]([CH3:6])[CH2:8][CH2:9]3)=[O:4])=[C:15]([CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[C:37]([F:40])([F:39])[F:38])[S:16][C:17]=2[N:18]([CH2:26][CH:27]([CH3:29])[CH3:28])[C:19]1=[O:25]

Participants

8

Reactant 4

HCID 13140Acryloyl chlorideHCID 531671-MethylpiperazineHCID 80271Tri-o-tolylphosphineHCID 114429025-Bromo-1-isobutyl-3-methyl-6-[2-(trifluoromethyl)benzyl]-thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

Product 1

HCID 69746631HCID 69746631, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Procedure

Acryloyl chloride (0.65 ml) was added dropwise to a solution of 1-methylpiperazine (0.94 ml) and triethylamine (2 ml) in acetonitrile (10 ml) in a pressure tube at 0° C. and stirred at room temperature for 1 hour. 5-Bromo-3-methyl-1-(2-methylpropyl)-6-[[2-(trifluoromethyl)phenyl]methyl]-thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (0.40 g, Example 1c)), palladium acetate (0.019 g) and tri-o-tolylphosphine (0.051 g) was added to the pressure tube and the reaction was heated at 70° C. for 21 hours. After cooling, the reaction mixture was concentrated under reduced pressure. The residue was purified by flash silica chromatography eluting with a gradient of 0-5% ethanol in dichloromethane to give a brown solid. The solid was triturated with acetonitrile to give the title compound as a white powder (0.042 g).

Workup

  1. temperaturethe reaction was heated at 70° C. for 21 hours
  2. temperatureAfter cooling
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. customThe residue was purified by flash silica chromatography
  5. washeluting with a gradient of 0-5% ethanol in dichloromethane
  6. customto give a brown solid
  7. customThe solid was triturated with acetonitrile

Sources & evidence

ORD record
ord-9dc8949d513c4b638de96c58784db24c
Source dataset
uspto-grants-2005_05
Patent number
US06890923B2

Reaction notes

Loading…