Bromocyclopentane → 4-Chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine

HRID 916752Notes

Reaction equation

[H-].[Na+].[Cl:3][C:4]1[C:5]2[CH:12]=[CH:11][NH:10][C:6]=2[N:7]=[CH:8][N:9]=1.[CH:13]1(Br)[CH2:17][CH2:16][CH2:15][CH2:14]1>CN(C=O)C>[Cl:3][C:4]1[C:5]2[CH:12]=[CH:11][N:10]([CH:13]3[CH2:17][CH2:16][CH2:15][CH2:14]3)[C:6]=2[N:7]=[CH:8][N:9]=1

Participants

Conditions

Temperature: 0 °C

Procedure

NaH (3.8 g, 95.3 mmol) was added to a solution of 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine (10 g, 63.5 mmol) in DMF (50 mL) at 0° C. The resulting mixture was stirred at 0° C. for 30 min, then warmed to room temperature. At this time Cyclopentylbromide (18.9 g, 127 mmol) was added and the reaction was heated to 60° C. After 4 h the reaction was cooled to 0° C. and quenched with water. The aqueous layer was extracted with EtOAc (3×), the combined organic layers were washed with water (1×), dried over Na2SO4, and concentrated. Purification by flash column chromatography (Hexanes/Ethyl acetate 9:1) afforded the title compound as a clear oil (10.6 g, 75%). MS: 222.1/224.1 (MH+); HPLC Rf: 5.77 min. (HPLC method 4).

Workup

temperaturewarmed to room temperature
temperaturethe reaction was heated to 60° C
temperatureAfter 4 h the reaction was cooled to 0° C.
customquenched with water
extractionThe aqueous layer was extracted with EtOAc (3×)
washthe combined organic layers were washed with water (1×)
dry with materialdried over Na2SO4
concentrationconcentrated
customPurification by flash column chromatography (Hexanes/Ethyl acetate 9:1)

Sources & evidence

ORD record: ord-3897007bb490444795291112d1f8c911
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07271262B2

Reaction notes

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