Citric Acid → HCID 71186280, compound

HRID 633632Notes

Reaction equation

HRID 633632 reaction equation
[CH2:1]([Mg]Br)[CH:2]([CH3:4])[CH3:3].Cl[C:8]1[C:9]2[N:24]=[C:23]([C:25]3[CH:30]=[C:29]([CH3:31])[C:28]([O:32][CH3:33])=[C:27]([CH3:34])[CH:26]=3)[O:22][C:10]=2[N:11]=[C:12]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[N:13]=1.C(OCC)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1.C/C(/[O-])=C/C(C)=O.C/C(/[O-])=C/C(C)=O.C/C(/[O-])=C/C(C)=O.[Fe+3]>[Cl:21][C:18]1[CH:17]=[CH:16][C:15]([CH2:14][C:12]2[N:13]=[C:8]([CH2:1][CH:2]([CH3:4])[CH3:3])[C:9]3[N:24]=[C:23]([C:25]4[CH:26]=[C:27]([CH3:34])[C:28]([O:32][CH3:33])=[C:29]([CH3:31])[CH:30]=4)[O:22][C:10]=3[N:11]=2)=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 311Citric AcidHCID 3283Diethyl EtherHCID 86675959HCID 86675959, compoundHCID 178418816HCID 178418816, compound

Product 1

HCID 71186280HCID 71186280, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 5483663Ferric acetylacetonateCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

Under argon and at 0° C., 2.0 ml of a 2.0 M solution of isobutylmagnesium bromide in tetrahydrofuran were slowly added dropwise to a degassed solution of 1.50 g of 7-chloro-5-(4-chlorobenzyl)-2-(4-methoxy-3,5-dimethylphenyl)oxazolo[5,4-d]pyrimidine and 65 mg of iron(III) acetylacetonate in 20 ml of dry tetrahydrofuran. After 15 min at 0° C., diethyl ether was added to the reaction mixture, and 10% strength aqueous citric acid solution was added with ice cooling. The phases were separated, and the aqueous phase was extracted twice with diethyl ether. The combined organic phases was washed with water, dried over sodium sulfate, filtered and concentrated under reduced pressure. From the crude product, 0.80 g (51%) of the title compound was isolated after reprecipitation from acetonitrile.

Workup

  1. additionwas added with ice cooling
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted twice with diethyl ether
  4. washThe combined organic phases was washed with water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-db3ce5c3def84491bdc828864e38e6d7
Source dataset
uspto-grants-2016_04
Patent number
US09321787B2

Reaction notes

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