Methylamine → HCID 58075560, compound

HRID 475810Notes

Reaction equation

HRID 475810 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]=[C:15]([F:17])[C:14](F)=[C:13]([F:19])[CH:12]=3)[C:6]=2[N:7]=1.[CH3:21][NH2:22]>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:12]=[C:13]([F:19])[CH:14]=[C:15]([F:17])[CH:16]=3)[C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 6329Methylamine2×HCID 58075300HCID 58075300, compound

Product 1

HCID 58075560HCID 58075560, compoundYield 30.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2,4-dichloro-7-(3,4,5-trifluorophenyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidine (498 mg, 1.561 mmol) and methanamine (1.561 mL, 3.12 mmol) in MeOH (10 mL) was stirred at rt for 1 h. Incomplete reaction was observed. Additional portions of methanamine (1.561 mL, 3.12 mmol) were added to the reaction mixture until the reaction was complete. The solvent was removed in vacuum and the residue was purified by column chromatography on silica gel to give 2-chloro-7-(3,5-difluorophenyl)-N-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-amine (60 mg, 0.203 mmol, 30.5% yield). LC-MS (M+H)+=314.0.

Workup

  1. customIncomplete reaction
  2. customThe solvent was removed in vacuum
  3. customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-a2debcff15d942259bbb4e896e626520
Source dataset
uspto-grants-2014_01
Patent number
US08637525B2

Reaction notes

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