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

HRID 1952779Notes

Reaction equation

HRID 1952779 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-c6687a4ac40241e48640c3f3c2906d88
Source dataset
uspto-grants-2000_09
Patent number
US06114339

Reaction notes

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