Acetic Acid → 2-Ethoxymethyl-6-methyl-4(3H)-pteridinone

HRID 326864Notes

Reaction equation

HRID 326864 reaction equation
N[C:2]1[C:11]2[C:6](=[N:7][CH:8]=[C:9]([CH3:12])[N:10]=2)[N:5]=[C:4]([CH2:13][O:14][CH2:15][CH3:16])[N:3]=1.C(O)(=[O:19])C>[OH-].[Na+]>[CH2:15]([O:14][CH2:13][C:4]1[NH:3][C:2](=[O:19])[C:11]2[C:6](=[N:7][CH:8]=[C:9]([CH3:12])[N:10]=2)[N:5]=1)[CH3:16]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 107275934-Amino-2-ethoxymethyl-6-methylpteridine

Product 1

HCID 1355283202-Ethoxymethyl-6-methyl-4(3H)-pteridinone

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent2×

Procedure

A suspension of 7.4 g (0.0338 mole) of 4-amino-2-ethoxymethyl-6-methylpteridine in 148 ml of 5% aqueous sodium hydroxide is brought slowly to 85° C. and maintained at this temperature for 2 hours. A further 592 ml of 5% aqueous sodium hydroxide are then added and heating is continued at 85° C for 1 hour. After cooling, the solution obtained is acidified with acetic acid to pH 5.5, and is then extracted with dichloromethane. The organic extracts are dried over sodium sulphate and concentrated to dryness under reduced pressure. The solid residue is recrystallized from acetone in the presence of Norit. Yld: 4.9 g (66%), m.p. 181°-183° C.

Workup

  1. customis brought slowly to 85° C.
  2. temperaturemaintained at this temperature for 2 hours
  3. temperatureheating
  4. temperatureAfter cooling
  5. customthe solution obtained
  6. extractionis then extracted with dichloromethane
  7. dry with materialThe organic extracts are dried over sodium sulphate
  8. concentrationconcentrated to dryness under reduced pressure
  9. customThe solid residue is recrystallized from acetone in the presence of Norit

Sources & evidence

ORD record
ord-94bb753b01c94866b5795133cfa7411e
Source dataset
uspto-grants-1993_12
Patent number
US05270465

Reaction notes

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