Water → cis-1-{[6-(4,4-Dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidin-4-yl]methyl}pyrrolidine-3,4-diol

HRID 2171811Notes

Reaction equation

CS(O[CH2:6][C:7]1[C:8]2[CH:16]=[C:15]([CH:17]3[CH2:22][CH2:21][C:20]([CH3:24])([CH3:23])[CH2:19][CH2:18]3)[S:14][C:9]=2[N:10]=[C:11]([CH3:13])[N:12]=1)(=O)=O.Cl.[NH:26]1[CH2:30][C@H:29]([OH:31])[C@H:28]([OH:32])[CH2:27]1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH3:23][C:20]1([CH3:24])[CH2:21][CH2:22][CH:17]([C:15]2[S:14][C:9]3[N:10]=[C:11]([CH3:13])[N:12]=[C:7]([CH2:6][N:26]4[CH2:30][C@H:29]([OH:31])[C@H:28]([OH:32])[CH2:27]4)[C:8]=3[CH:16]=2)[CH2:18][CH2:19]1

Participants

Conditions

Temperature: 50 °C

Procedure

A suspension of [6-(4,4-dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidin-4-yl]methyl methanesulfonate (100 mg), cis-pyrrolidine-3,4-diol hydrochloride (57 mg), and K2CO3 (75 mg) in DMF (3 mL) was stirred at 50° C. for 12 hours. The reaction mixture was cooled to room temperature, and water was added thereto, followed by extraction with EtOAc. The organic layer was dried over MgSO4 and then concentrated under reduced pressure. The residue was purified by silica gel column (chloroform/MeOH). The obtained purified product was suspended in IPE, and the precipitate was collected by filtration to obtain cis-1-{[6-(4,4-dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidin-4-yl]methyl}pyrrolidine-3,4-diol (9 mg).

Workup

temperatureThe reaction mixture was cooled to room temperature
extractionfollowed by extraction with EtOAc
dry with materialThe organic layer was dried over MgSO4
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column (chloroform/MeOH)
customThe obtained purified product
filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record: ord-1421a5473a564f64af0dde8e02e88006
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09051339B2

Reaction notes

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