Hydrochloric Acid → 7-[(4,6-Dimethoxy-pyrimidin-2-yl)oxy]-3-hydroxy-phthalide

HRID 22159

Reaction equation

HRID 22159 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([O:11][C:12]2[CH:13]=[CH:14][CH:15]=[C:16]3[C:21]=2[C:19](=[O:20])[O:18][CH:17]3[O:22]C)[N:4]=1.Cl>O1CCCC1>[CH3:10][O:9][C:7]1[CH:8]=[C:3]([O:2][CH3:1])[N:4]=[C:5]([O:11][C:12]2[CH:13]=[CH:14][CH:15]=[C:16]3[C:21]=2[C:19](=[O:20])[O:18][CH:17]3[OH:22])[N:6]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 199273827-[(4,6-Dimethoxy-pyrimidin-2-yl)oxy]-3-methoxyphthalide

Product 1

HCID 199274177-[(4,6-Dimethoxy-pyrimidin-2-yl)oxy]-3-hydroxy-phthalide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

15.2 g of 7-[(4,6-dimethoxy-pyrimidin-2-yl)oxy]-3-methoxyphthalide (see Example 8) are heated at reflux temperature in a 1:1 mixture of tetrahydrofuran and hydrochloric acid for 3 hours. Concentration is then carried out under reduced pressure and the resulting crystals are filtered off and washed with water to yield pure 7-[(4,6-dimethoxy-pyrimidin-2-yl)oxy]-3-hydroxy-phthalide, m.p. 143°-145° C.; IR (KBr): 1770 cm-1 ; 1H-NMR (CDCl3): 6.60 ppm (s, 1H).

Workup

  1. temperatureat reflux temperature
  2. concentrationConcentration
  3. filtrationthe resulting crystals are filtered off
  4. washwashed with water

Sources & evidence

ORD record
ord-e000064620014360bd4ff23c9d507bc0
Source dataset
uspto-grants-1995_06
Patent number
US05428002

Linked notes

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