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N,N-Dimethylaniline → 4-Chloro-3-(2-chloroethyl)-8-mesityl-2,6-dimethylimidazo[1,5-a]pyrimidine

HRID 890188
Notes
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Reaction equation

HRID 890188 reaction equation
[Cl:1][CH2:2][CH2:3][C:4]1[C:5]([CH3:24])=[N:6][C:7]2[N:8]([C:11]([CH3:23])=[N:12][C:13]=2[C:14]2[C:19]([CH3:20])=[CH:18][C:17]([CH3:21])=[CH:16][C:15]=2[CH3:22])[C:9]=1O.CN(C)C1C=CC=CC=1.NC(CC)CC.O.P(Cl)(Cl)([Cl:43])=O>C(#N)C>[Cl:43][C:9]1[N:8]2[C:11]([CH3:23])=[N:12][C:13]([C:14]3[C:19]([CH3:20])=[CH:18][C:17]([CH3:21])=[CH:16][C:15]=3[CH3:22])=[C:7]2[N:6]=[C:5]([CH3:24])[C:4]=1[CH2:3][CH2:2][Cl:1]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 949N,N-DimethylanilineHCID 962WaterHCID 120193-PentanamineHCID 24813Phosphorus oxychlorideHCID 178424660HCID 178424660, compound

Product 1

HCID 222495154-Chloro-3-(2-chloroethyl)-8-mesityl-2,6-dimethylimidazo[1,5-a]pyrimidine

Reagents, catalysts & solvents

1
HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 3-(2-chloroethyl)-8-mesityl-2,6-dimethylimidazo[1,5-a]pyrimidin-4-ol (200 mg, 0.58 mmol) and N,N-dimethylaniline (0.3 mL) in phosphorus oxychloride (3 mL) was heated under reflux for six hours. After overnight, 3-aminopentane (2 mL) was added to a solution of the residue in acetonitrile (5 mL), followed by stirring at 80° C. for three hours. Water was added, and the mixture was extracted with ethyl acetate, washed with brine, dried over anhydrous magnesium sulfate and evaporated. The residue was purified by silica gel column chromatogrpahy (10-20% ethyl acetate/hexane), to give the title compound (139 mg) as pale yellow crystals.

Workup

  1. temperatureunder reflux for six hours
  2. extractionthe mixture was extracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated
  6. customThe residue was purified by silica gel column chromatogrpahy (10-20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-dc3bf8e5e199409bb7476d1a151333b4
Source dataset
uspto-grants-2006_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06995163B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes