Diisopropyl Ether → HCID 57494528, compound

HRID 222615Notes

Reaction equation

HRID 222615 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([NH2:7])[CH:3]=1.C([O:11]/[C:12](/[C:22](OC)=[O:23])=[C:13](/OC(=O)C)\[C:14]([O:16][CH3:17])=[O:15])(=O)C.C(OC(C)C)(C)C>C1(C)C=CC(S(O)(=O)=O)=CC=1.C(O)C>[CH3:17][O:16][C:14]([C:13]1[N:7]=[C:4]2[CH:3]=[C:2]([CH3:1])[O:6][N:5]2[C:22](=[O:23])[C:12]=1[OH:11])=[O:15]

Participants

6

Reactant 3

HCID 7914Diisopropyl EtherHCID 661723-Amino-5-methylisoxazoleHCID 13100501HCID 13100501, compound

Product 1

HCID 57494528HCID 57494528, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

5-Methyl-isoxazol-3-ylamine (392 mg, 3.99 mmol), dimethyl diacetoxyfumarate (1.04 g, 3.99 mmol) and p-toluenesulphonic acid (10 mg) were combined in a capped vial and heated to 100° C. After 5 h the reaction was cooled to room temperature and ethanol (2.5 mL) and iso-propyl ether (2.5 mL) was added to the residue which was sonicated for 15 min. The resulting precipitate collected by filtration and washed with cold ethanol (5 mL) and dried on the pump to afford 6-hydroxy-2-methyl-7-oxo-7H-isoxazolo[2,3-a]pyrimidine-5-carboxylic acid methyl ester (331 mg, 37%): 1H NMR (300 MHz, D6DMSO) δ 2.50 (3H, s, CH3), 3.84 (3H, s, OCH3), 6.67 (1H, s, H3), 10.31 (1H, br s, OH).

Workup

  1. temperatureAfter 5 h the reaction was cooled to room temperature
  2. customwas sonicated for 15 min
  3. filtrationThe resulting precipitate collected by filtration
  4. washwashed with cold ethanol (5 mL)
  5. customdried on the pump

Sources & evidence

ORD record
ord-154fbb734666452193530a8b64e624da
Source dataset
uspto-grants-2012_06
Patent number
US08207334B2

Reaction notes

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