2-Butyn-1-ol → HCID 66594504, compound
Reaction equation
[H-].[Na+].[CH2:3]([OH:7])[C:4]#[C:5][CH3:6].Cl[C:9]1[N:14]=[CH:13][N:12]=[C:11]([N:15]2[C@H:20]([CH3:21])[CH2:19][CH2:18][CH2:17][C@@H:16]2[CH3:22])[C:10]=1[F:23].[Cl-].[NH4+]>O1CCCC1>[CH2:3]([O:7][C:9]1[C:10]([F:23])=[C:11]([N:15]2[C@H:20]([CH3:21])[CH2:19][CH2:18][CH2:17][C@@H:16]2[CH3:22])[N:12]=[CH:13][N:14]=1)[C:4]#[C:5][CH3:6]Participants
Procedure
0.05 g of sodium hydride (60% oil suspention) was suspended in 2 ml of tetrahydrofuran. 0.3 ml of tetrahydrofuran solution of 0.09 g of 2-butyn-1-ol was added dropwise at room temperature therein, and the mixture was stirred for 10 minutes. Into the mixture was added dropwise 0.3 ml of tetrahydrofuran solution of 0.21 g of 6-chloro-4-(cis-2,6-dimethylpiperidino)-5-fluoropyrimidine at room temperature, and stirred for 6 hours at 60° C. After the reaction mixture was cooled to near room temperature, the reaction mixture was poured into a saturated ammonium chloride aqueous solution, and the mixture was extracted with tert-butyl methyl ether three times. The organic layers were washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.21 g of 4-(2-butynyloxy)-6-(cis-2,6-dimethylpiperidino)-5-fluoropyrimidine (hereinafter, referred to as Compound (49)).
Workup
- stirringstirred for 6 hours at 60° C
- extractionthe mixture was extracted with tert-butyl methyl ether three times
- washThe organic layers were washed with a saturated sodium chloride aqueous solution
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-ade0735af21447b0bfec714d0bdc3359
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08129526B2
Reaction notes
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