1-Naphthalenecarbonyl chloride → 3-Methyl-1-(2-methylpropyl)-6-(1-naphthalenylcarbonyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

HRID 1251597Notes

Reaction equation

HRID 1251597 reaction equation
[C:1]1([C:11](Cl)=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[Cl-].[Al+3].[Cl-].[Cl-].[CH3:18][N:19]1[C:24](=[O:25])[C:23]2[CH:26]=[CH:27][S:28][C:22]=2[N:21]([CH2:29][CH:30]([CH3:32])[CH3:31])[C:20]1=[O:33]>ClCCCl>[CH3:18][N:19]1[C:24](=[O:25])[C:23]2[CH:26]=[C:27]([C:11]([C:1]3[C:10]4[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=4)[CH:4]=[CH:3][CH:2]=3)=[O:12])[S:28][C:22]=2[N:21]([CH2:29][CH:30]([CH3:31])[CH3:32])[C:20]1=[O:33]

Participants

5

Reactant 3

HCID 701461-Naphthalenecarbonyl chlorideHCID 52825273-Methyl-1-(2-methylpropyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dioneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 222579723-Methyl-1-(2-methylpropyl)-6-(1-naphthalenylcarbonyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

1-Naphthoyl chloride (1.25 ml) was added under nitrogen to a stirred slurry of aluminium chloride (1.1 g) in 1,2-dichloroethane (10 ml). A solution of 3-methyl-1-(2-methylpropyl)thieno[2,3-d]pyrimidin-2,4(1H,3H)-dione (2.0 g) in 1,2-dichloroethane (10 ml) was added dropwise and the resultant mixture was heated under reflux for 24 h and then allowed to cool to ambient temperature. The reaction mixture was quenched by the careful addition of water (2 ml) and was then concentrated in vacuo. The residue was dissolved in ethyl acetate and washed thrice with dilute hydrochloric acid, twice with saturated sodium hydrogen carbonate solution, and once with brine, then dried over magnesium sulfate and concentrated in vacuo. Purification by chromatography on silica gel eluting with toluene:ethyl acetate (9:1) gave the title compound (0.78 g).

Workup

  1. temperatureunder reflux for 24 h
  2. customThe reaction mixture was quenched by the careful addition of water (2 ml)
  3. concentrationwas then concentrated in vacuo
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed thrice with dilute hydrochloric acid
  6. dry with materialtwice with saturated sodium hydrogen carbonate solution, and once with brine, then dried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customPurification by chromatography on silica gel eluting with toluene:ethyl acetate (9:1)

Sources & evidence

ORD record
ord-f64991cab6fb4e08bfb4c2065d5ea067
Source dataset
uspto-grants-2002_01
Patent number
US06342502B1

Reaction notes

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