1-Propanol → HCID 86643680, compound

HRID 1514347Notes

Reaction equation

HRID 1514347 reaction equation
[Br:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4](Cl)[N:3]=1.CO[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([NH2:20])[CH:15]=1.C([N:23](CC)CC)C.[CH2:28]([OH:31])CC>>[Br:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4]([N:20]([O:31][CH3:28])[C:16]2[CH:15]=[CH:14][CH:19]=[CH:18][CH:17]=2)[N:3]=1.[BrH:1].[NH3:23]

Participants

7

Reactant 4

HCID 10311-PropanolHCID 8471TriethylamineHCID 108243-MethoxyanilineHCID 52877442-Bromo-6-chloro-9H-purine

Product 3

HCID 222AmmoniaYield 10%HCID 260Hydrogen BromideHCID 86643680HCID 86643680, compoundYield 69%

Procedure

2-Bromo-6-(methoxyanilino)purine was prepared in a similar manner to example 5 by the reaction of 2-bromo-6-chloropurine and m-anisidine (molar ratio 1:1) in the presence of triethylamine (2.5 eq.) in n-propanol at 100° C. for 4 hours. After cooling to room temperature the resulting white precipitate was filtered off, washed with cold n-propanol and water and dried in desiccator into constant weight. Yield: 69% (as hydrobromide). Crude product was purified by crystallization from methanol and free base was obtained by treatment of hydrobromide with 10% aqueous ammonia. HPLC purity: 98+%.

Workup

  1. filtrationwas filtered off
  2. washwashed with cold n-propanol and water
  3. customdried in desiccator into constant weight
  4. customCrude product was purified by crystallization from methanol

Sources & evidence

ORD record
ord-ab860093ac784458940d7c16ee37f3fe
Source dataset
uspto-grants-2012_07
Patent number
US08222260B2

Reaction notes

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