3-Fluoropyrrolidine → 2-chloro-7-(4-fluorophenyl)-4-((R)-3-fluoropyrrolidin-1-yl)-6,7-dihydro-5H cyclopenta[d]pyrimidine

HRID 451047Notes

Reaction equation

HRID 451047 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])=[CH:13][CH:12]=3)[C:6]=2[N:7]=1.[F:19][C@@H:20]1[CH2:24][CH2:23][NH:22][CH2:21]1>>[Cl:1][C:2]1[N:3]=[C:4]([N:22]2[CH2:23][CH2:24][C@@H:20]([F:19])[CH2:21]2)[C:5]2[CH2:10][CH2:9][CH:8]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[C:6]=2[N:7]=1

Participants

3

Reactant 2

HCID 27591633-FluoropyrrolidineHCID 580754242,4-Dichloro-7-(4-fluorophenyl)-6,7-dihydro-5H-cyclopenta[D]pyrimidine

Product 1

HCID 580754122-chloro-7-(4-fluorophenyl)-4-((R)-3-fluoropyrrolidin-1-yl)-6,7-dihydro-5H cyclopenta[d]pyrimidine

Procedure

2,4-dichloro-7-(4-fluorophenyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidine (Preparation H) was reacted as described in Preparation Hp1 and Hp2 with (R)-3-fluoropyrrolidine. The solvent was removed and the residue applied to Silica gel and eluted with an EtOAc/Hex gradient to afford the combined two diasteriomers (Hq). Ha1: LC-MS (M+H)+=336.0.

Workup

  1. customThe solvent was removed
  2. washeluted with an EtOAc/Hex gradient
  3. customto afford the

Sources & evidence

ORD record
ord-908165e3e8d94576bdf49ee94aa6a4c3
Source dataset
uspto-grants-2013_07
Patent number
US08486952B2

Reaction notes

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