Hydrochloric Acid → HCID 57929461, compound

HRID 2386665Notes

Reaction equation

C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:20]([C:23]1[C:32]2[CH:31]=[N:30][C:29]([S:33][CH3:34])=[N:28][C:27]=2[N:26]([CH:35]2[CH2:39][CH2:38][CH2:37][CH2:36]2)[C:25](=[O:40])[CH:24]=1)=[N+]=[N-].Cl.C([O-])(O)=O.[Na+]>C1COCC1>[NH2:20][C:23]1[C:32]2[CH:31]=[N:30][C:29]([S:33][CH3:34])=[N:28][C:27]=2[N:26]([CH:35]2[CH2:39][CH2:38][CH2:37][CH2:36]2)[C:25](=[O:40])[CH:24]=1

Participants

Conditions

Temperature: 35 °C

Procedure

Triphenylphosphine (1.68 g, 6.40 mmol) was added, at RT, to a solution of 5-azido-8-cyclopentyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one (1.29 g, 4.27 mmol) in THF (43 mL) and the reaction mixture was stirred at 35° C. for 2 h. An HCl (1 M, 22 mL) was then added and the reaction mixture was heated at reflux for 2 h and then was stored at 4° C. overnight. The resulting mixture was neutralized to pH 8 with NaHCO3 (sat'd aq), and was extracted with EtOAc (2×200 mL). The combined organic layers were dried over MgSO4, filtered and evaporated under reduced pressure. The crude residue was purified by flash chromatography (from 2 to >5% MeOH/DCM in 20 min.) to give 0.89 g (75% yield) of 5-amino-8-cyclopentyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one as a yellow solid. MS=277 [M+1]+.

Workup

temperaturethe reaction mixture was heated
temperatureat reflux for 2 h
waitwas stored at 4° C. overnight
extractionwas extracted with EtOAc (2×200 mL)
dry with materialThe combined organic layers were dried over MgSO4
filtrationfiltered
customevaporated under reduced pressure
customThe crude residue was purified by flash chromatography (from 2 to >5% MeOH/DCM in 20 min.)

Sources & evidence

ORD record: ord-7c00f7cc83794e87b4a5c34115f36b03
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08268840B2

Reaction notes

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