Diglyme → HCID 178527889, compound

HRID 853291Notes

Reaction equation

HRID 853291 reaction equation
P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:2].C(=O)(O)[O-].[Na+].COCCOCCOC.[C:29]1([C:35]2[NH:44][C:38]3[N:39]=[CH:40][N:41]=[C:42](O)[C:37]=3[CH:36]=2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>O>[C:29]1([C:35]2[NH:44][C:38]3[N:39]=[CH:40][N:41]=[C:42]([SH:2])[C:37]=3[CH:36]=2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 8150DiglymeHCID 14817Phosphorus sulfide (P2S5)3×HCID 516892Sodium Bicarbonate3×HCID 178518053HCID 178518053, compound

Product 1

HCID 178527889HCID 178527889, compoundYield 94.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

After adding 6.19 g of phosphorus pentasulfide, 6.24 g of sodium bicarbonate and 25 ml of diglyme to 2.45 g of the 6-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ol described in WO97/02266 and PCT/EP96/02728, and stirring the mixture for 1 hour, an additional 3 g of phosphorus pentasulfide and 3 g of sodium bicarbonate were added and the mixture was stirred for 1 hour. There were further added another 3 g of phosphorus pentasulfide and 3 g of sodium bicarbonate, and the mixture was stirred for 1 hour. It was then returned to room temperature, water was added, the mixture was stirred for 10 minutes, and the precipitated crystals were filtered out, washed with water and dried to obtain 2.5 g of the title compound.

Workup

  1. stirringthe mixture was stirred for 1 hour
  2. stirringthe mixture was stirred for 1 hour
  3. customwas then returned to room temperature
  4. stirringthe mixture was stirred for 10 minutes
  5. filtrationthe precipitated crystals were filtered out
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-e0d3c8386c854c3398b4131a0ec5a529
Source dataset
uspto-grants-2007_08
Patent number
US07253286B2

Reaction notes

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