Sodium Azide → 2-{4-[2-(2-Azidoethyl)cyclopropyl]piperidin-1-yl}-5-chloropyrimidine

HRID 1039104Notes

Reaction equation

CC1C=CC(S(O[CH2:12][CH2:13][C@H:14]2[CH2:16][C@@H:15]2[CH:17]2[CH2:22][CH2:21][N:20]([C:23]3[N:28]=[CH:27][C:26]([Cl:29])=[CH:25][N:24]=3)[CH2:19][CH2:18]2)(=O)=O)=CC=1.[N-:30]=[N+:31]=[N-:32].[Na+]>O1CCOCC1.O>[N:30]([CH2:12][CH2:13][CH:14]1[CH2:16][CH:15]1[CH:17]1[CH2:22][CH2:21][N:20]([C:23]2[N:28]=[CH:27][C:26]([Cl:29])=[CH:25][N:24]=2)[CH2:19][CH2:18]1)=[N+:31]=[N-:32]

Participants

Conditions

Temperature: 100 °C

Procedure

2-{2-[1-(5-chloropyrimidin-2-yl)piperidin-4-yl]cyclopropyl}ethyl 4-methylbenzenesulfonate from step 1 of this example (309 mg, 0.709 mmol) was in 5.67 mL dioxane. NaN3 (106 mg, 1.63 mmol) was added, followed by addition of 1.418 mL water. Reaction mixture was stirred at 100° C. for 2.5 hours before cooled back to room temperature. The reaction mixture was diluted with water and aqueous phase was further extracted with ethyl acetate for 3 times. The combined organic layers were washed with water and brine, then dried over Na2SO4 and concentrated. The residue was purified by column chromatography using gradient elution (0 to 30% ethyl acetate in hexane) to give the titled compound.

Workup

customReaction mixture
temperaturebefore cooled back to room temperature
extractionwas further extracted with ethyl acetate for 3 times
washThe combined organic layers were washed with water and brine
dry with materialdried over Na2SO4
concentrationconcentrated
customThe residue was purified by column chromatography
washelution (0 to 30% ethyl acetate in hexane)

Sources & evidence

ORD record: ord-0d492512034448b08f505859c6ad01f6
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08552022B2

Reaction notes

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