Triethylamine → Anisiflupurin

HRID 1514343Notes

Reaction equation

HRID 1514343 reaction equation
[F:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4](Cl)[N:3]=1.[CH3:12][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([NH2:20])[CH:15]=1.C(N(CC)CC)C>C(O)CCC>[F:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4]([NH:20][C:16]2[CH:17]=[CH:18][CH:19]=[C:14]([O:13][CH3:12])[CH:15]=2)[N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 108243-MethoxyanilineHCID 52879146-Chloro-2-fluoropurine

Product 1

HCID 25169483Anisiflupurin

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

This compound was prepared by the reaction of 2-fluoro-6-chloropurine (1.7 g; 0.01 mol), m-anisidine (1.23 g; 0.01 mol) and triethylamine (3.5 ml; 0.025 mol) in n-butanol (20 ml) at 90° C. for 4 hours. The reaction mixture was then cooled to the room temperature. The white precipitate was filtered off, rinsed with n-butanol (3×10 ml) and water (3×10 ml) and dried in the drying oven into constant weight. Yield: 5.55 g (61%) of yellowish crystalline powder. TLC (chloroform-methanol; 85:15): one single spot. HPLC purity: 99+%.

Workup

  1. filtrationThe white precipitate was filtered off
  2. washrinsed with n-butanol (3×10 ml) and water (3×10 ml)
  3. customdried in the drying oven into constant weight

Sources & evidence

ORD record
ord-34384f2066574ba39d9ddedf65812a8a
Source dataset
uspto-grants-2012_07
Patent number
US08222260B2

Reaction notes

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