Aniline → HCID 68473434, compound

HRID 1514345Notes

Reaction equation

HRID 1514345 reaction equation
[CH3:1][S:2][C:3]1[N:11]=[C:10]2[C:6]([NH:7][CH:8]=[N:9]2)=[C:5](Cl)[N:4]=1.[NH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(N(CC)CC)C>C(O)CCC>[CH3:1][S:2][C:3]1[N:11]=[C:10]2[C:6]([NH:7][CH:8]=[N:9]2)=[C:5]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:4]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 8471TriethylamineHCID 112641216-Chloro-2-(methylsulfanyl)-7H-purine

Product 1

HCID 68473434HCID 68473434, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

2-methylthio-6-chloropurine (10 g, 50 mmol), aniline (7.7 g, 63 mmol) and triethylamine (35 ml, 250 mmol) were refluxed in butanol (400 ml) for 2 h. Butanol was removed in vacuo and water (290 ml) added to the cooled residue. pH was adjusted to 8.0, the mixture was left at −16° C. overnight. Filtration and drying over phosphorus pentoxide in vacuo gave 10 g crude yellow-green product. The product was chromatographically purified (250 g silica, Fisons, chloroform); eluted with chloroform/methanol (97/3, v/v). Appropriate fractions were dried in vacuo, re-crystallised from ethanol with decolourisation by active carbon. After drying to constant weight over P2O5, yield 5.76 g, (46%), HPLC purity >98%. TLC: chloroform/methanol (9/1, v/v), no contaminants.

Workup

  1. customButanol was removed in vacuo and water (290 ml)
  2. additionadded to the cooled residue
  3. filtrationFiltration
  4. dry with materialdrying over phosphorus pentoxide in vacuo
  5. customgave 10 g crude yellow-green product
  6. customThe product was chromatographically purified (250 g silica, Fisons, chloroform)
  7. washeluted with chloroform/methanol (97/3
  8. customAppropriate fractions were dried in vacuo
  9. customre-crystallised from ethanol with decolourisation by active carbon
  10. dry with materialAfter drying to constant weight over P2O5, yield 5.76 g, (46%), HPLC purity >98%

Sources & evidence

ORD record
ord-ee6cbfc6383d429c99359f77b4f44ad9
Source dataset
uspto-grants-2012_07
Patent number
US08222260B2

Reaction notes

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