2-Butyn-1-ol → HCID 69429823, compound

HRID 1592223Notes

Reaction equation

HRID 1592223 reaction equation
[H-].[Na+].[CH2:3]([OH:7])[C:4]#[C:5][CH3:6].Cl[C:9]1[CH:14]=[C:13]([O:15][C@@H:16]2[CH2:21][CH2:20][CH2:19][CH2:18][C@@H:17]2[CH3:22])[N:12]=[CH:11][N:10]=1.[Cl-].[NH4+]>O1CCCC1>[CH2:3]([O:7][C:9]1[CH:14]=[C:13]([O:15][C@@H:16]2[CH2:21][CH2:20][CH2:19][CH2:18][C@@H:17]2[CH3:22])[N:12]=[CH:11][N:10]=1)[C:4]#[C:5][CH3:6]

Participants

6

Reactant 4

HCID 129912-Butyn-1-olHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 86591870HCID 86591870, compound

Product 1

HCID 69429823HCID 69429823, compoundYield 72.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

In 1 ml of tetrahydrofuran was suspended 0.03 g of sodium hydride (60% in oil), to which 0.2 ml of a tetrahydrofuran solution containing 0.04 g of 2-butyn-1-ol was slowly added dropwise under stirring at room temperature. The mixture was stirred at room temperature for 20 minutes, and 0.2 ml of a tetrahydrofuran solution containing 0.12 g of 4-chloro-6-(cis-2-methylcyclohexyloxy)pyrimidine was slowly added dropwise, followed by stirring at room temperature for 5 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution and extracted three times with t-butyl methyl ether. The organic layers were combined, washed with water, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography to give 0.10 g of 4-(2-butynyloxy)-6-(cis-2-methylcyclohexyloxy)pyrimidine (the present compound (172)).

Workup

  1. additionwas slowly added dropwise
  2. stirringThe mixture was stirred at room temperature for 20 minutes
  3. additionwas slowly added dropwise
  4. stirringby stirring at room temperature for 5 hours
  5. extractionextracted three times with t-butyl methyl ether
  6. washwashed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-457f27ee63084ce0820e19240e47e2c8
Source dataset
uspto-grants-2007_11
Patent number
US07291730B2

Reaction notes

Loading…