Hydrochloric Acid → HCID 57929480, compound
Reaction equation
C(N(C(C)C)CC)(C)C.C1CCN2C(=NCCC2)CC1.C([O:23][C:24](=O)[CH2:25][C:26]([C:28]1[C:29]([NH:36][CH:37]2[CH2:41][CH2:40][CH2:39][CH2:38]2)=[N:30][C:31]([S:34][CH3:35])=[N:32][CH:33]=1)=[O:27])C.Cl>CCOC(C)=O>[CH:37]1([N:36]2[C:29]3[N:30]=[C:31]([S:34][CH3:35])[N:32]=[CH:33][C:28]=3[C:26]([OH:27])=[CH:25][C:24]2=[O:23])[CH2:41][CH2:40][CH2:39][CH2:38]1Participants
6
Conditions
- Temperature
- 120 °C
Procedure
Diisopropylethylamine (12 mL) and DBU (1.62 mL) were added to 3-(4-cyclopentylamino-2-methylsulfanyl-pyrimidin-5-yl)-3-oxo-propionic acid ethyl ester (3.0 g, 9.29 mmol) and the resulting mixture was heated to 120° C. for 1 h. The reaction mixture was then cooled to RT and acidified with HCl (1 M aq) to pH 1. The resulting mixture was diluted with EtOAc and washed 3× with HCl (1 M aq). The combined aqueous layers were extracted with EtOAc and then 3× with a 1:1 mixture of isopropanol and chloroform. The combined organic extracts were dried over Na2SO4, filtered and evaporated under reduced pressure to afford 2.5 g (97% yield) of 8-cyclopentyl-5-hydroxy-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one.
Workup
- temperatureThe reaction mixture was then cooled to RT
- washwashed 3× with HCl (1 M aq)
- extractionThe combined aqueous layers were extracted with EtOAc
- addition3× with a 1:1 mixture of isopropanol and chloroform
- dry with materialThe combined organic extracts were dried over Na2SO4
- filtrationfiltered
- customevaporated under reduced pressure
Sources & evidence
- ORD record
- ord-dfaaf0203a984c2fae1032145ae2715a
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08268840B2
Reaction notes
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