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Water → 5-Allyl-4-chloro-6-(2,4-dichloroanilino)-2-methylpyrimidine

HRID 1860435
Notes
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Reaction equation

HRID 1860435 reaction equation
[H-].[Na+].[CH2:3]([C:6]1[C:7](Cl)=[N:8][C:9]([CH3:13])=[N:10][C:11]=1[Cl:12])[CH:4]=[CH2:5].[Cl:15][C:16]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:17]=1[NH2:18].O>CN(C=O)C>[CH2:3]([C:6]1[C:11]([Cl:12])=[N:10][C:9]([CH3:13])=[N:8][C:7]=1[NH:18][C:17]1[CH:19]=[CH:20][C:21]([Cl:23])=[CH:22][C:16]=1[Cl:15])[CH:4]=[CH2:5]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 111232,4-DichloroanilineHCID 24758Sodium hydrideHCID 130708374,6-Dichloro-2-methyl-5-(prop-2-en-1-yl)pyrimidine

Product 1

HCID 121134695-Allyl-4-chloro-6-(2,4-dichloroanilino)-2-methylpyrimidineYield 37%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

Sodium hydride mineral oil dispersion (60%, 1.38 g, 34.5 mmol) was added to a stirred solution of pyrimidine (10) (3.50 g, 17.2 mmol) and 2,4-dichloroaniline (3.07 g, 18.9 mmol) in DMF (40 mL). After 25 min, the mixture was poured into water (100 mL) and extracted with dichloromethane. The combined extracts were dried (MgSO4), concentrated under vacuum, and the residue was chromatographed (elution with dichloromethane) to afford 2.09 g (37%) of pyrimidine (11) as a white powder.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe combined extracts were dried (MgSO4)
  3. concentrationconcentrated under vacuum
  4. customthe residue was chromatographed
  5. wash(elution with dichloromethane)

Sources & evidence

ORD record
ord-5659a9b573e4438aaa733f7ff40632bb
Source dataset
uspto-grants-2003_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06531475B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes