Diisopropylethylamine → HCID 58075755, compound

HRID 2370162Notes

Reaction equation

HRID 2370162 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.C[CH2:21][N:22](C(C)C)C(C)C>CO>[Cl:1][C:2]1[N:3]=[C:4]([NH:22][CH3:21])[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 81531DiisopropylethylamineHCID 58075298HCID 58075298, compound

Product 1

HCID 58075755HCID 58075755, compoundYield 37.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2,4-dichloro-7-(3,4-difluorophenyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidine (421 mg, 1.398 mmol), methanamine, HCl (283 mg, 4.19 mmol) and DIPEA (1.465 mL, 8.39 mmol) in methanol (10 mL) was stirred at rt for 1 h. 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-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-amine (154 mg, 0.521 mmol, 37.2% yield). LC-MS (M+H)+=296.2.

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-016b4f7c938041b9a0d230df285486eb
Source dataset
uspto-grants-2014_04
Patent number
US08710061B2

Reaction notes

Loading…