Ammonium Chloride → HCID 22599735, compound

HRID 1759934Notes

Reaction equation

HRID 1759934 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([C:10]1[CH:15]=[C:14]([O:16][CH2:17][C:18]#[C:19][CH3:20])[N:13]=[CH:12][N:11]=1)=[O:9].[CH3:21][Li].[Cl-].[NH4+]>O1CCCC1>[CH2:17]([O:16][C:14]1[CH:15]=[C:10]([C:8]([OH:9])([CH3:21])[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])[N:11]=[CH:12][N:13]=1)[C:18]#[C:19][CH3:20]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 22599685HCID 22599685, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 22599735HCID 22599735, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

In 3.7 ml of tetrahydrofuran was dissolved 0.4 g of 6-(2-butynyloxy)pyrimidin-4-yl 2-fluorophenyl ketone, to which 3.6 ml (1.14 mol/l diethyl ether solution) of methyl lithium was added dropwise at −78° C. After stirring at −78° C. for 3 hours, the reaction mixture was poured into a saturated aqueous ammonium chloride solution and extracted three times with ethyl acetate. The organic layers were combined and washed with a saturated aqueous sodium chloride solution, and the combined organic layer was dried over anhydrous magnesium sulfate and then concentrated. The residue was subjected to silica gel column chromatography to give 0.34 g of 4-(2-butynyloxy)-6-(α-hydroxy-α-methyl-2-fluorobenzyl)pyrimidine (the present compound (157)).

Workup

  1. extractionextracted three times with ethyl acetate
  2. washwashed with a saturated aqueous sodium chloride solution
  3. dry with materialthe combined organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-26fb977a6bcb432183372cb3916797c3
Source dataset
uspto-grants-2005_01
Patent number
US06838463B2

Reaction notes

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