Sodium hydride → HCID 86614305, compound

HRID 469870Notes

Reaction equation

HRID 469870 reaction equation
[NH2:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([Cl:9])[N:3]=1.[F:10][C:11]([F:27])([F:26])[CH:12]([C:14]1[CH:23]=[CH:22][C:21]2[C:16](=[CH:17][CH:18]=[C:19]([O:24][CH3:25])[CH:20]=2)[CH:15]=1)[OH:13].[H-].[Na+]>O1CCOCC1>[Cl:9][C:4]1[CH:5]=[C:6]([O:13][CH:12]([C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[C:19]([O:24][CH3:25])[CH:20]=3)[CH:15]=2)[C:11]([F:26])([F:27])[F:10])[N:7]=[C:2]([NH2:1])[N:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 655222-Amino-4,6-dichloropyrimidineHCID 11230594HCID 11230594, compound

Product 1

HCID 86614305HCID 86614305, compoundYield 104.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

2-Amino 4,6-dichloro pyrimidine (0.096 g, 0.6 mmol), 2,2,2-trifluoro-1-(6-methoxy-naphthalen-2-yl)-ethanol (0.140 g, 0.55 mmol), and NaH (96 mg, 0.60 mmol) were added to anhydrous dioxane (20 ml) under a nitrogen atmosphere. The reaction was stirred at 80° C. for 12 hours, cooled to room temperature, and quenched with water (0.2 ml). The reaction mixture was concentrated, and the residue dissolved in CH2Cl2 (50 ml), washed with water (20 ml), brine (20 ml) dried (Na2SO4) and concentrated to afford the crude intermediate, 4-chloro-6-[2,2,2-trifluoro-1-(6-methoxy-naphthalene-2-yl)-ethoxy]-pyrimidin-2-ylamine (0.22 g) which was directly used in the following step.

Workup

  1. temperaturecooled to room temperature
  2. customquenched with water (0.2 ml)
  3. concentrationThe reaction mixture was concentrated
  4. dissolutionthe residue dissolved in CH2Cl2 (50 ml)
  5. washwashed with water (20 ml), brine (20 ml)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a2ac67cb31c14e1ab2012260352b2b18
Source dataset
uspto-grants-2014_01
Patent number
US08629156B2

Reaction notes

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