Sulfuric Acid → HCID 21934411, compound

HRID 1241351Notes

Reaction equation

HRID 1241351 reaction equation
[C:1]([C:3]1[C:4]([NH2:25])=[N:5][C:6]([NH2:24])=[N:7][C:8]=1[O:9][CH2:10][CH2:11][O:12][CH2:13][P:14]([O:20][CH:21]([CH3:23])[CH3:22])([O:16][CH:17]([CH3:19])[CH3:18])=[O:15])#N.S(=O)(=O)(O)[OH:27]>O.[Pd]>[CH:1]([C:3]1[C:4]([NH2:25])=[N:5][C:6]([NH2:24])=[N:7][C:8]=1[O:9][CH2:10][CH2:11][O:12][CH2:13][P:14]([O:20][CH:21]([CH3:23])[CH3:22])([O:16][CH:17]([CH3:19])[CH3:18])=[O:15])=[O:27]

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 21934409HCID 21934409, compound

Product 1

HCID 21934411HCID 21934411, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

5-Cyano-2,4-diamino-6-[2-(diisopropoxyphosphorylmethoxy)ethoxy]pyrimidine (1.5 g, 4 mmol) was hydrogenated in water (36 ml) and sulfuric acid (6 ml) over 5% palladium on charcoal (0.25 g) under stirring for 20 h at room temperature. The mixture was filtered through a pad of Celite and the catalyst was washed with hot water and hot methanol (100 ml each). The filtrate was neutralized with aqueous NaOH and solvents evaporated. The residue was mixed with hot methanol, salts were filtered off and the mixture was taken down. Product was purified by column chromatography on silica gel (elution with 3% MeOH in CHCl3) to give 0.63 g (42%) of 5-formyl-2,4-diamino-6-[2-(diisopropoxyphosphorylmethoxy)ethoxy]pyrimidine.

Workup

  1. filtrationThe mixture was filtered through a pad of Celite
  2. washthe catalyst was washed with hot water and hot methanol (100 ml each)
  3. customevaporated
  4. additionThe residue was mixed with hot methanol, salts
  5. filtrationwere filtered off
  6. customProduct was purified by column chromatography on silica gel (elution with 3% MeOH in CHCl3)

Sources & evidence

ORD record
ord-cdaf6d01b79a4172a001eb312e60433f
Source dataset
uspto-grants-2006_10
Patent number
US07115592B2

Reaction notes

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