Bromine → HCID 15838748, compound

HRID 617800Notes

Reaction equation

HRID 617800 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:18])=[CH:10][CH:9]=2)[CH:5]=[C:4]([CH:19]([CH3:21])[CH3:20])[N:3]=1.[Br:22]Br.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)(Cl)Cl.[Fe]>[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:18])=[CH:10][CH:9]=2)[C:5]([Br:22])=[C:4]([CH:19]([CH3:21])[CH3:20])[N:3]=1

Participants

6

Reactant 3

HCID 24408BromineHCID 1969684-(4-Fluoro-1-naphthalenyl)-6-(1-methylethyl)-2-pyrimidinamineHCID 516892Sodium Bicarbonate

Product 1

HCID 15838748HCID 15838748, compoundYield 56.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 2-amino-4-(4-fluoronaphth-1-yl)-6-isopropylpyrimidine (free base, 0.100 g) in carbon tetrachloride (10 mL) was added iron powder (0.002 g) and bromine (0.074 g) at room temperature. The reaction mixture was stirred at room temperature for 1 hour, after which time it was poured into sodium bicarbonate solution (saturated, 30 mL). The layers were separated and the aqueous layer was extracted three times with methylene chloride (3×10 mL). The combined organic layers were evaporated to dryness. The residue was purified by preparative thin layer chromatography, eluting with hexane/ethyl acetate, and recrystallized from ether/hexane to give 2-amino-5-bromo-4-(4-fluoronaphth-1-yl)-6-isopropylpyrimidine (0.072 g), m.p. 176-180° C.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted three times with methylene chloride (3×10 mL)
  3. customThe combined organic layers were evaporated to dryness
  4. customThe residue was purified by preparative thin layer chromatography
  5. washeluting with hexane/ethyl acetate
  6. customrecrystallized from ether/hexane

Sources & evidence

ORD record
ord-fd3dbb20e8a344779fb755abad5efb16
Source dataset
uspto-grants-1999_09
Patent number
US05952331

Reaction notes

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