Water → 2-Amino-4-(4-aminonaphth-1-yl)-6-isopropylpyrimidine

HRID 617802Notes

Reaction equation

HRID 617802 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](F)=[CH:10][CH:9]=2)[CH:5]=[C:4]([CH:19]([CH3:21])[CH3:20])[N:3]=1.[N-:22]=[N+]=[N-].[Na+].O>CN1C(=O)CCC1>[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([NH2:22])=[CH:10][CH:9]=2)[CH:5]=[C:4]([CH:19]([CH3:21])[CH3:20])[N:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 1969684-(4-Fluoro-1-naphthalenyl)-6-(1-methylethyl)-2-pyrimidinamine

Product 1

HCID 218464362-Amino-4-(4-aminonaphth-1-yl)-6-isopropylpyrimidineYield 53%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

2-Amino-4-(4-fluoronaphth-1-yl)-6-isopropyl-pyrimidine (0.288 g) was dissolved in N-methy pyrrolidinone (5 mL) and sodium azide (0.288 g) was added. The mixture was brought to a temperature of 160° C. under an inert atmosphere for 16 hours. After cooling the reaction mixture was poured into water (50 mL) and the reaction product was extracted with ethyl acetate (3×30 mL). The organic layer was dried over sodium sulfate and evaporated to dryness. The product was purified by column chromatography on silica gel, eluting with hexane/ethyl acetate, and recrystallized from tert-butyl methyl ether to give 2-amino-4-(4-aminonaphth-1-yl)-6-isopropylpyrimidine (0.151 g), m.p. 185-186° C.

Workup

  1. temperatureAfter cooling the reaction mixture
  2. extractionthe reaction product was extracted with ethyl acetate (3×30 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customevaporated to dryness
  5. customThe product was purified by column chromatography on silica gel
  6. washeluting with hexane/ethyl acetate
  7. customrecrystallized from tert-butyl methyl ether

Sources & evidence

ORD record
ord-f0eedfd418354b498141892651c6da9a
Source dataset
uspto-grants-1999_09
Patent number
US05952331

Reaction notes

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