Azetidine → HCID 58075537, compound

HRID 2370166Notes

Reaction equation

HRID 2370166 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]([O:17][C:18]([F:21])([F:20])[F:19])=[CH:13][CH:12]=3)[C:6]=2[N:7]=1.[NH:23]1[CH2:26][CH2:25][CH2:24]1>CO>[N:23]1([C:4]2[C:5]3[CH2:10][CH2:9][CH:8]([C:11]4[CH:16]=[CH:15][C:14]([O:17][C:18]([F:21])([F:20])[F:19])=[CH:13][CH:12]=4)[C:6]=3[N:7]=[C:2]([Cl:1])[N:3]=2)[CH2:26][CH2:25][CH2:24]1

Participants

4

Reactant 2

HCID 10422AzetidineHCID 58075561HCID 58075561, compound

Product 1

HCID 58075537HCID 58075537, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2,4-dichloro-7-(4-(trifluoromethoxy)phenyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidine (250 mg, 0.716 mmol) and azetidine (82 mg, 1.432 mmol) in MeOH (3 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 4-(azetidin-1-yl)-2-chloro-7-(4-(trifluoromethoxy)phenyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidine (238 mg, 0.644 mmol, 90% yield). LC-MS (M+H)+=371.2.

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-d42b59de70b8405d9ed0967e259e4f54
Source dataset
uspto-grants-2014_04
Patent number
US08710061B2

Reaction notes

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