Azetidine → 4-(azetidin-1-yl)-2-chloro-7-phenyl-6,7-dihydro-5H-cyclopenta[d]pyrimidine

HRID 2370104Notes

Reaction equation

HRID 2370104 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][CH:14]=[CH:13][CH:12]=3)[C:6]=2[N:7]=1.[NH:18]1[CH2:21][CH2:20][CH2:19]1>CO>[N:18]1([C:4]2[C:5]3[CH2:10][CH2:9][CH:8]([C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=4)[C:6]=3[N:7]=[C:2]([Cl:1])[N:3]=2)[CH2:21][CH2:20][CH2:19]1

Participants

4

Reactant 2

HCID 10422AzetidineHCID 580754632,4-Dichloro-7-phenyl-6,7-dihydro-5H-cyclopenta[D]pyrimidine

Product 1

HCID 580754924-(azetidin-1-yl)-2-chloro-7-phenyl-6,7-dihydro-5H-cyclopenta[d]pyrimidineYield 100.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2,4-dichloro-7-phenyl-6,7-dihydro-5H-cyclopenta[d]pyrimidine (150 mg, 0.566 mmol) and excess azetidine (162 mg, 2.83 mmol) in methanol (1 mL) was stirred at rt for 30 min. The solvent was removed in vacuum to afford 4-(azetidin-1-yl)-2-chloro-7-phenyl-6,7-dihydro-5H-cyclopenta[d]pyrimidine (162 mg, 0.567 mmol, 100% yield). LC-MS (M+H)+=286.3.

Workup

  1. customThe solvent was removed in vacuum

Sources & evidence

ORD record
ord-59c33667cb0843dab31316652b63ea08
Source dataset
uspto-grants-2014_04
Patent number
US08710061B2

Reaction notes

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