Guanidine Hydrochloride → 2,4-Diamino-6-(2,3-dihydro-3-hydroxy-2,2-dimethylbenzofuran-7-yl)pteridine

HRID 440913Notes

Reaction equation

HRID 440913 reaction equation
C[O-].[Na+].Cl.[NH2:5][C:6]([NH2:8])=[NH:7].N[C:10]1[C:15]([C:16]#[N:17])=[N:14][C:13]([C:18]2[C:26]3[O:25][C:24]([CH3:28])([CH3:27])[CH:23]([OH:29])[C:22]=3[CH:21]=[CH:20][CH:19]=2)=[CH:12][N:11]=1>CO>[NH2:7][C:6]1[N:8]=[C:16]([NH2:17])[C:15]2[C:10](=[N:11][CH:12]=[C:13]([C:18]3[C:26]4[O:25][C:24]([CH3:27])([CH3:28])[CH:23]([OH:29])[C:22]=4[CH:21]=[CH:20][CH:19]=3)[N:14]=2)[N:5]=1

Participants

5

Reactant 3

HCID 5742Guanidine HydrochlorideHCID 10942334Sodium MethoxideHCID 190407832-Amino-3-cyano-5-(2,3-dihydro-3-hydroxy-2,2-dimethylbenzofuran-7-yl)pyrazine

Product 1

HCID 190407812,4-Diamino-6-(2,3-dihydro-3-hydroxy-2,2-dimethylbenzofuran-7-yl)pteridine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2.8 grams (0.052 mole) of sodium methoxide in 100 mL of methanol is stirred, and 1.9 grams (0.019 mole) of guanidine hydrochloride is added. Upon completion of addition, the reaction mixture is stirred for about 5 minutes and then is filtered to remove sodium chloride. The filtrate is then added to 4.5 grams (0.016 mole) of 2-amino-3-cyano-5-(2,3-dihydro-3-hydroxy-2,2-dimethylbenzofuran-7-yl)pyrazine. The stirring reaction mixture is then heated to reflux where it is stirred for about 18 hours. After this time the reaction mixture is cooled and filtered. The filter cake is washed with water and dried, yielding 2,4-diamino-6-(2,3-dihydro-3-hydroxy-2,2-dimethylbenzofuran-7-yl)pteridine.

Workup

  1. additionUpon completion of addition
  2. filtrationis filtered
  3. customto remove sodium chloride
  4. customThe stirring reaction mixture
  5. temperatureis then heated
  6. temperatureto reflux where it
  7. stirringis stirred for about 18 hours
  8. temperatureAfter this time the reaction mixture is cooled
  9. filtrationfiltered
  10. washThe filter cake is washed with water
  11. customdried

Sources & evidence

ORD record
ord-8d9ea533c8bb4ed99b1280a5ea45f09a
Source dataset
uspto-grants-1996_05
Patent number
US05521190

Reaction notes

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