2-Butyn-1-ol → 4-(2-Butynyloxy)-6-(cis-2,6-dimethylpiperidino)pyrimidine

HRID 1008711Notes

Reaction equation

HRID 1008711 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])[CH:10]=1.[Cl-].[NH4+]>O1CCCC1>[CH2:3]([O:7][C:9]1[CH:10]=[C:11]([N:15]2[C@H:16]([CH3:22])[CH2:17][CH2:18][CH2:19][C@@H:20]2[CH3:21])[N:12]=[CH:13][N:14]=1)[C:4]#[C:5][CH3:6]

Participants

6

Reactant 4

HCID 129912-Butyn-1-olHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 866074664-Chloro-6-(cis-2,6-dimethylpiperidino)pyrimidine

Product 1

HCID 665946224-(2-Butynyloxy)-6-(cis-2,6-dimethylpiperidino)pyrimidineYield 91.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

0.06 g of sodium hydride (60% oil suspension) was suspended in 1.5 ml of tetrahydrofuran. 0.3 ml of tetrahydrofuran solution of 0.08 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 0.19 g of 6-chloro-4-(cis-2,6-dimethylpiperidino)pyrimidine 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 0.20 g of 4-(2-butynyloxy)-6-(cis-2,6-dimethylpiperidino)pyrimidine (hereinafter, referred to as Compound (48)).

Workup

  1. stirringstirred for 6 hours at 60° C
  2. extractionthe mixture was extracted with tert-butyl methyl ether three times
  3. washThe organic layers were washed with a saturated sodium chloride aqueous solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5520b37c9d444cce829943d38f98a380
Source dataset
uspto-grants-2011_07
Patent number
US07973028B2

Reaction notes

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