Dimethyl Sulfoxide → 2,4-Diamino-6-(2,3-dihydro-2,2-dimethyl-3-benzofuranon-7-yl)pteridine

HRID 1734171Notes

Reaction equation

HRID 1734171 reaction equation
CS(C)=O.[NH2:5][C:6]1[N:15]=[C:14]([NH2:16])[C:13]2[C:8](=[N:9][CH:10]=[C:11]([C:17]3[C:25]4[O:24][C:23]([CH3:27])([CH3:26])[CH:22]([OH:28])[C:21]=4[CH:20]=[CH:19][CH:18]=3)[N:12]=2)[N:7]=1.C(N(CC)CC)C.O>C(Cl)Cl>[NH2:5][C:6]1[N:15]=[C:14]([NH2:16])[C:13]2[C:8](=[N:9][CH:10]=[C:11]([C:17]3[C:25]4[O:24][C:23]([CH3:26])([CH3:27])[C:22](=[O:28])[C:21]=4[CH:20]=[CH:19][CH:18]=3)[N:12]=2)[N:7]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 8471TriethylamineHCID 190407812,4-Diamino-6-(2,3-dihydro-3-hydroxy-2,2-dimethylbenzofuran-7-yl)pteridine

Product 1

HCID 867495132,4-Diamino-6-(2,3-dihydro-2,2-dimethyl-3-benzofuranon-7-yl)pteridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-60 °C

Procedure

A stirring solution of 1.8 grams (0.011 mole) of pyridine-sulfur trioxide complex [prepared by the method of E. E. Gilbert, Chem. Rev., 62, 551-555 (1962)] in 25 mL of methylene chloride is cooled to -60° C., and a solution of 2.0 grams (0.024 mole) of dimethyl sulfoxide in 5 mL of methylene chloride is added dropwise during a 5 minute period. Upon completion of addition, the reaction mixture is stirred at -60° C. for about 10 minutes. After this time a solution of 3.2 grams (0.10 mole) of 2,4-diamino-6-(2,3-dihydro-3-hydroxy-2,2-dimethylbenzofuran-7-yl)pteridine in 10 mL of methylene chloride is added dropwise during a 5 minute period. Upon completion of addition, the reaction mixture is again stirred at -60° C. for about 10 minutes, and then 5.1 grams (0.050 mole) of triethylamine is added dropwise during a 5 minute period. The reaction mixture is then allowed to warm to ambient temperature. After this time 30 mL of water is added, and the mixture is stirred for about 10 minutes. The aqueous layer is separated and extracted with about 20 mL of methylene chloride. The extract is combined with the organic layer, and the combination is concentrated under reduced pressure, yielding 2,4-diamino-6-(2,3-dihydro-2,2-dimethyl-3-benzofuranon-7-yl)pteridine.

Workup

  1. customA stirring solution of 1.8 grams (0.011 mole) of pyridine-sulfur trioxide complex [prepared by the method of E
  2. additionUpon completion of addition
  3. additionUpon completion of addition
  4. stirringthe reaction mixture is again stirred at -60° C. for about 10 minutes
  5. temperatureto warm to ambient temperature
  6. stirringthe mixture is stirred for about 10 minutes
  7. customThe aqueous layer is separated
  8. extractionextracted with about 20 mL of methylene chloride
  9. concentrationthe combination is concentrated under reduced pressure

Sources & evidence

ORD record
ord-0dece1fce56a4f798dcd3a6b7b8dc3bd
Source dataset
uspto-grants-1996_07
Patent number
US05532367

Reaction notes

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