Chloroacetaldehyde → (R)-3-chloro-5-cyclopentyl-6-ethyl-5,6-dihydroimidazo[1,2-f]pteridine

HRID 39339

Reaction equation

HRID 39339 reaction equation
[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[N:8]=[C:7]([NH2:12])[C@@H:6]([CH2:13][CH3:14])[N:5]([CH:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)[C:4]=2[N:3]=1.Cl[CH2:21][CH:22]=O.C([O-])(O)=O.[Na+].CCOC(C)=O>CO>[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[N:8]3[CH:21]=[CH:22][N:12]=[C:7]3[C@@H:6]([CH2:13][CH3:14])[N:5]([CH:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)[C:4]=2[N:3]=1

Participants

6

Reactant 4

HCID 33Chloroacetaldehyde2×HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 59389593(R)-2-chloro-8-cyclopentyl-7-ethyl-7,8-dihydropteridin-6-amine

Product 1

HCID 59389590(R)-3-chloro-5-cyclopentyl-6-ethyl-5,6-dihydroimidazo[1,2-f]pteridine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
68 °C

Procedure

(R)-2-chloro-8-cyclopentyl-7-ethyl-7,8-dihydropteridin-6-amine (177 mg, 0.64 mmol) in MeOH (1.5 mL) treated with 50% aqueous chloroacetaldehyde (131 μL, 1.3 Eq.) and the reaction mixture heated to reflux for 6 hours. A further portion of 50% aq. chloroacetaldehyde (400 μL, 3.0 Eq.) was added, and the reaction mixture heated to 68° C. overnight. NaHCO3 (aq. sat.) and EtOAc was added, and the aqueous was further extracted with EtOAc. The combined organic extracts were dried over MgSO4, filtered and concentrated in vacuo.

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureto reflux for 6 hours
  3. extractionthe aqueous was further extracted with EtOAc
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3e1e8996efa2489aa28b5ccb4882deb3
Source dataset
uspto-grants-2013_09
Patent number
US08524902B2

Linked notes

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