1-Naphthalenemethanol → 6-Chloro-2-(1-naphthylmethoxy)pyrimidin-4-amine

HRID 1602182

Reaction equation

HRID 1602182 reaction equation
[C:1]1([CH2:11][OH:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[NH2:15][C:16]1[CH:21]=[C:20]([Cl:22])[N:19]=[C:18](Cl)[N:17]=1>C1COCC1>[NH2:15][C:16]1[CH:21]=[C:20]([Cl:22])[N:19]=[C:18]([O:12][CH2:11][C:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=[CH:3][CH:2]=2)[N:17]=1

Participants

5

Reactant 3

HCID 209081-NaphthalenemethanolHCID 24758Sodium hydrideHCID 823874-Pyrimidinamine, 2,6-dichloro-

Product 1

HCID 4705086-Chloro-2-(1-naphthylmethoxy)pyrimidin-4-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-Naphthalenemethanol (227 mg, 1.44 mmol) is added to a slurry of 50% sodium hydride (69 mg, 1.44 mmol) in dry THF (4 ml) at 0° C. After stirring for 30 minutes, 4-amino-2,6-dichloropyrimidine (157 mg, 0.96 mmol) is added and stirred at 22° C. for 72 hours. The solution is quenched with saturated NH4Cl and concentrated in vacuo. The residue is dissolved in methylene chloride and washed 3× saturated NaHCO3, dried with MgSO4, filtered, and concentrated in vacuo. The sample is purified by chromatography using 1:2 ethyl acetate/hexanes and recrystallization from heptane/toluene, mp 160-161° C.

Workup

  1. stirringstirred at 22° C. for 72 hours
  2. customThe solution is quenched with saturated NH4Cl
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue is dissolved in methylene chloride
  5. washwashed 3× saturated NaHCO3
  6. dry with materialdried with MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe sample is purified by chromatography
  10. custom1:2 ethyl acetate/hexanes and recrystallization from heptane/toluene, mp 160-161° C.

Sources & evidence

ORD record
ord-fb5c01d00e954664a2426336b92669f7
Source dataset
uspto-grants-1999_11
Patent number
US05981537

Linked notes

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