Citric Acid → HCID 58016880, compound

HRID 1926897Notes

Reaction equation

HRID 1926897 reaction equation
[CH3:1][C:2]([CH3:7])([CH2:5][OH:6])[CH2:3][OH:4].Cl[C:9]1[C:10]2[C:17]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=3)=[C:16]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[O:15][C:11]=2[N:12]=[CH:13][N:14]=1.ClCCl.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1.O>[CH3:25][O:24][C:21]1[CH:20]=[CH:19][C:18]([C:17]2[C:10]3[C:9]([O:4][CH2:3][C:2]([CH3:7])([CH3:1])[CH2:5][OH:6])=[N:14][CH:13]=[N:12][C:11]=3[O:15][C:16]=2[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 311Citric AcidHCID 6344DichloromethaneHCID 31344Neopentyl glycolHCID 580168154-Chloro-5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidine

Product 1

HCID 58016880HCID 58016880, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Put 1.546 g (14.85 mmol) 2,2-dimethylpropane-1,3-diol in 30 ml THF. Add 833 mg (7.42 mmol) potassium tert.-butylate and stir for a further 15 min at RT. Then cool to 0° C. and add a solution of 1.00 g (2.97 mmol) 4-chloro-5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidine in 15 ml THF dropwise over a time of 30 min. Leave to return to RT and stir for a further 30 min at RT. Then add dichloromethane and water, acidify with 10% citric acid solution and separate the phases. Extract the aqueous phase once with dichloromethane. Combine the organic phases and wash once with satd. sodium chloride solution, dry over magnesium sulphate and concentrate by evaporation. 1.20 g (99.9% of theor.) of the target compound is obtained.

Workup

  1. temperatureThen cool to 0° C.
  2. customLeave
  3. customto return to RT
  4. stirringstir for a further 30 min at RT
  5. customseparate the phases
  6. extractionExtract the aqueous phase once with dichloromethane
  7. washwash once with satd
  8. dry with materialsodium chloride solution, dry over magnesium sulphate
  9. concentrationconcentrate by evaporation
  10. custom1.20 g (99.9% of theor.) of the target compound is obtained

Sources & evidence

ORD record
ord-5850fff812ba4e12b50fd377360ee2c7
Source dataset
uspto-grants-2012_05
Patent number
US08183246B2

Reaction notes

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