2-Ethylpyrrolidine → 2-chloro-4-(2-ethylpyrrolidin-1-yl)-7-(4-fluorophenyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidine

HRID 451040Notes

Reaction equation

HRID 451040 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.[CH2:19]([CH:21]1[CH2:25][CH2:24][CH2:23][NH:22]1)[CH3:20]>>[Cl:1][C:2]1[N:3]=[C:4]([N:22]2[CH2:23][CH2:24][CH2:25][CH:21]2[CH2:19][CH3:20])[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 49934652-EthylpyrrolidineHCID 580754242,4-Dichloro-7-(4-fluorophenyl)-6,7-dihydro-5H-cyclopenta[D]pyrimidine

Product 1

HCID 580754522-chloro-4-(2-ethylpyrrolidin-1-yl)-7-(4-fluorophenyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidineYield 32%

Procedure

2,4-dichloro-7-(4-fluorophenyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidine (Preparation H) (200 mg, 0.706 mmol) and 2-ethylpyrrolidine (84 mg, 0.848 mmol) were combined and purified as per Preparation Hd to give two pairs of racemic diasteriomers 2-chloro-4-(2-ethylpyrrolidin-1-yl)-7-(4-fluorophenyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidine. (Hf1, Diastereomer 1, racemic, first to elute) (77 mg, 0.223 mmol, 32% yield) LC-MS (M+H)+=346. (Hf2, Diastereomer 2, racemic, second to elute) (80 mg, 0.232 mmol, 33% yield); LC-MS (M+H)+=346.2. The relative stereochemistry for Hf1 and Hf2 was not determined

Workup

  1. custompurified as per Preparation Hd

Sources & evidence

ORD record
ord-adac397c08a8480fb70b902de3e7e311
Source dataset
uspto-grants-2013_07
Patent number
US08486952B2

Reaction notes

Loading…