Toluene → 4-Chloro-6-(4,4-dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidine

HRID 2171774Notes

Reaction equation

[CH3:1][C:2]1([CH3:19])[CH2:7][CH2:6][CH:5]([C:8]2[S:18][C:11]3[N:12]=[C:13]([CH3:17])[NH:14][C:15](=O)[C:10]=3[CH:9]=2)[CH2:4][CH2:3]1.C1(C)C=CC=CC=1.P(Cl)(Cl)([Cl:29])=O>CN(C=O)C>[Cl:29][C:15]1[C:10]2[CH:9]=[C:8]([CH:5]3[CH2:6][CH2:7][C:2]([CH3:19])([CH3:1])[CH2:3][CH2:4]3)[S:18][C:11]=2[N:12]=[C:13]([CH3:17])[N:14]=1

Participants

Conditions

Temperature: 130 °C

Procedure

To a mixture of 6-(4,4-dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidin-4(3H)-one (30.0 g) and toluene (240 mL) were added phosphorous oxychloride (40 mL) and DMF (1.0 mL), followed by heating to reflux at 130° C. for 2 hours. The reaction mixture was left to be cooled to room temperature and concentrated under reduced pressure. To the residue were added chloroform and saturated aqueous sodium bicarbonate, followed by stirring. The organic layer was washed sequentially with water and brine. To the organic layer were added MgSO4, activated carbon (10 g), and silica gel (100 mL), followed by stirring. The mixture was filtered through Celite and then concentrated under reduced pressure to obtain 4-chloro-6-(4,4-dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidine (31.3 g).

Workup

temperatureby heating
waitThe reaction mixture was left
temperatureto be cooled to room temperature
concentrationconcentrated under reduced pressure
additionTo the residue were added chloroform and saturated aqueous sodium bicarbonate
washThe organic layer was washed sequentially with water and brine
additionTo the organic layer were added MgSO4, activated carbon (10 g), and silica gel (100 mL)
stirringby stirring
filtrationThe mixture was filtered through Celite
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-09228ea538484cdfaaacc9d6e64c77ed
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09051339B2

Reaction notes

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