Tetrahydrofuran → HCID 403201, compound

HRID 2237403Notes

Reaction equation

HRID 2237403 reaction equation
[CH3:1][O-:2].[Na+].[CH2:4]([NH:11][C:12]1[N:21]=[C:20]2[C:15]([C:16]([N:35]3CCCC3)=[N:17][C:18]([N:22]3[CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][CH2:23]3)=[N:19]2)=[N:14][C:13]=1Cl)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.O1[CH2:45][CH2:44][CH2:43][CH2:42]1>>[CH2:4]([NH:11][C:12]1[N:21]=[C:20]2[C:15]([C:16]([N:35]3[CH2:42][CH2:43][CH2:44][CH2:45]3)=[N:17][C:18]([N:22]3[CH2:23][CH2:24][NH:25][CH2:26][CH2:27]3)=[N:19]2)=[N:14][C:13]=1[O:2][CH3:1])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 10942334Sodium MethoxideHCID 86605196HCID 86605196, compound

Product 1

HCID 403201HCID 403201, compound

Procedure

100 mg (1.76 mmol) sodium methoxide and 300 mg (0.571 mmol) tert.butyl 4-(7-benzylamino-6-chloro-4-pyrrolidin-1-yl-pteridin-2-yl)-piperazine-1- carboxylate are suspended in 5 ml of tetrahydrofuran, then placed in the microwave for 0.1 hours at 120° C. Then the reaction mixture is concentrated by evaporation, the residue is combined with methanol and suction filtered. The mother liquor is concentrated by evaporation, then extracted with water and dichloromethane. The organic phase is dried and evaporated to dryness. The residue is purified by chromatography. Corresponding fractions are concentrated by evaporation and crystallised from diethyl ether.

Workup

  1. concentrationThen the reaction mixture is concentrated by evaporation
  2. filtrationfiltered
  3. concentrationThe mother liquor is concentrated by evaporation
  4. extractionextracted with water and dichloromethane
  5. customThe organic phase is dried
  6. customevaporated to dryness
  7. customThe residue is purified by chromatography
  8. concentrationCorresponding fractions are concentrated by evaporation
  9. customcrystallised from diethyl ether

Sources & evidence

ORD record
ord-1b0cdf523afe49179b1983d87cbf4e88
Source dataset
uspto-grants-2010_05
Patent number
US07718654B2

Reaction notes

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