Acetic Anhydride → (2,4-Dihydroxypyrido[3,2-d]pyrimidin-6-yl)methyl acetate

HRID 1597829Notes

Reaction equation

HRID 1597829 reaction equation
[O:1]=[C:2]1[NH:7][C:6]2[CH:8]=[CH:9][C:10]([CH3:12])=[N:11][C:5]=2[C:4](=[O:13])[NH:3]1.C1C=C(Cl)C=[C:16]([C:21]([O:23]O)=[O:22])C=1.C(OC(=O)C)(=O)C>C(O)(=O)C>[C:21]([O:23][CH2:12][C:10]1[CH:9]=[CH:8][C:6]2[NH:7][C:2](=[O:1])[NH:3][C:4](=[O:13])[C:5]=2[N:11]=1)(=[O:22])[CH3:16]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 70297m-Chloroperbenzoic acidHCID 2732402499-96-9

Product 1

HCID 22281841(2,4-Dihydroxypyrido[3,2-d]pyrimidin-6-yl)methyl acetateYield 66%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1.77 g of 1 (10 mmol) in 50 ml of glacial acetic acid containing 6.5 g of MCPBA (57-85%) was refluxed for 3 hours. Acetic anhydride (40 ml) was added to the hot reaction mixture and the refluxing was continued for another half an hour. The clear brown solution was evaporated to dryness and the solid was stirred with ether (100 ml) and filtered. The solid was crystallized from ethanol to give 1.55 g (66%) of 2.

Workup

  1. waitthe refluxing was continued for another half an hour
  2. customThe clear brown solution was evaporated to dryness
  3. filtrationfiltered
  4. customThe solid was crystallized from ethanol

Sources & evidence

ORD record
ord-409e710302ed4ad9b46bafe5c3a98d3f
Source dataset
uspto-grants-1998_04
Patent number
US05736547

Reaction notes

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