Water → HCID 66658981, compound

HRID 333667Notes

Reaction equation

HRID 333667 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([OH:9])=[CH:4][N:3]=1.[H-].[Na+].C1N=CN([C:17](N2C=NC=C2)=[O:18])C=1.O>CN(C=O)C>[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[O:9][C:17](=[O:18])[NH:8][C:6]=2[N:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 682631,1'-CarbonyldiimidazoleHCID 131268512,4-Diaminopyrimidin-5-ol

Product 1

HCID 66658981HCID 66658981, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

2,4-Diamino-pyrimidin-5-ol (500 mg, 3.97 mmol) [prepared according to the method of Hull. J. Chem. Soc. 1956, 2033-2035] was suspended in DMF (10 mL). To this was added consecutively NaH (86.7 mg, 3.77 mmol) and CDI (707 mg, 4.36 mmol), and the reaction mixture was heated with vigorous stirring at 60° C. for 3 h. The mixture was cooled to ambient temperature, and then quenched with water (25 mL). The solvent and water were removed via rotary evaporation, and the residue was then triturated in water (5 mL). The solid was then collected by filtration and dried, affording 230 mg (38%): 1H NMR (400 MHz, d6-DMSO) δ 11.90 (br s, 1H), 7.72 (br s, 1H), 6.72 (s, 2H); Analysis calc'd for C5H4N4O2.0.2; H2O: C, 38.56; H, 2.85; N, 35.98. Found: C, 39.01; H, 2.71; N, 35.58; [M+H]+ m/z 153.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureThe mixture was cooled to ambient temperature
  3. customquenched with water (25 mL)
  4. customThe solvent and water were removed via rotary evaporation
  5. customthe residue was then triturated in water (5 mL)
  6. filtrationThe solid was then collected by filtration
  7. customdried
  8. customaffording 230 mg (38%)

Sources & evidence

ORD record
ord-6ca75f567d094d66be7490f527430b9b
Source dataset
uspto-grants-2014_11
Patent number
US08883758B2

Reaction notes

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