Butanal → HCID 86662664, compound

HRID 2278876Notes

Reaction equation

HRID 2278876 reaction equation
[Cl:1][C:2]1[N:10]=[C:9](I)[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH3:12].C([Mg]Cl)(C)C.[CH:18](=[O:22])[CH2:19][CH2:20][CH3:21].[NH4+].[Cl-]>C1COCC1>[Cl:1][C:2]1[N:10]=[C:9]([CH:18]([OH:22])[CH2:19][CH2:20][CH3:21])[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH3:12]

Participants

6

Reactant 4

HCID 261ButanalHCID 25517Ammonium ChlorideHCID 10803775HCID 10803775, compoundHCID 178418918HCID 178418918, compound

Product 1

HCID 86662664HCID 86662664, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 6-chloro-2-iodo-9-methyl-9H-purine (3.7 g, 12.6 mmol) in anhydrous THF (48 ml) at −78° C. under an atmosphere of nitrogen was added isopropylmagnesium chloride (8 ml, 15.12 mmol). After 30 minutes butyraldehyde (1.7 ml, 16.38 mmol) was added at −78° C. dropwise. The reaction mixture was stirred at −78° C. for 8 h and then allowed to warm to RT overnight. The reaction was quencend with a saturated solution of NH4Cl. The aqueous phase was extracted with DCM (three times). The organic phases were dried over anhydrous sodium sulphate and evaporated under reduced pressure. The residue was purified by flash chromatography (gradient DCM/MeOH: 98/2 to DCM/MeOH: 96/4).

Workup

  1. temperatureto warm to RT overnight
  2. extractionThe aqueous phase was extracted with DCM (three times)
  3. dry with materialThe organic phases were dried over anhydrous sodium sulphate
  4. customevaporated under reduced pressure
  5. customThe residue was purified by flash chromatography (gradient DCM/MeOH: 98/2 to DCM/MeOH: 96/4)

Sources & evidence

ORD record
ord-d164ca60ae344c60b0424a382a2d63c6
Source dataset
uspto-grants-2015_09
Patent number
US09133197B2

Reaction notes

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