Dimethylamine → HCID 58075738, compound

HRID 475795Notes

Reaction equation

HRID 475795 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[CH2:10][CH2:9][CH:8]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[C:13]([F:18])[CH:12]=3)[C:6]=2[N:7]=1.[CH3:20][NH:21][CH3:22]>CO>[Cl:1][C:2]1[N:3]=[C:4]([N:21]([CH3:22])[CH3:20])[C:5]2[CH2:10][CH2:9][CH:8]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[C:13]([F:18])[CH:12]=3)[C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 58075298HCID 58075298, compound

Product 1

HCID 58075738HCID 58075738, compoundYield 31.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2,4-dichloro-7-(3,4-difluorophenyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidine (446 mg, 1.481 mmol) and excess dimethylamine (2.222 mL, 4.44 mmol) in MeOH (6 mL) was stirred at rt for 30 min. The solvent was removed in vacuum and the crude product was purified by column chromatography on silica gel to afford 2-chloro-7-(3,4-difluorophenyl)-N,N-dimethyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-amine (146 mg, 0.471 mmol, 31.8% yield). LC-MS (M+H)+=310.2.

Workup

  1. customThe solvent was removed in vacuum
  2. customthe crude product was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-dfaa5dfc0cb44bf7846503815ce6b7d2
Source dataset
uspto-grants-2014_01
Patent number
US08637525B2

Reaction notes

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