Acetyl chloride → HCID 59835021, compound

HRID 271273Notes

Reaction equation

HRID 271273 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[CH2:5][N:6]1[CH:14]=[N:13][C:12]2[C:7]1=[N:8][C:9]([NH2:20])=[N:10][C:11]=2[C:15]1[O:16][CH:17]=[CH:18][CH:19]=1.[C:24](Cl)(=[O:26])[CH3:25]>N1C=CC=CC=1>[C:24]([NH:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[CH2:5][N:6]1[CH:14]=[N:13][C:12]2[C:7]1=[N:8][C:9]([NH2:20])=[N:10][C:11]=2[C:15]1[O:16][CH:17]=[CH:18][CH:19]=1)(=[O:26])[CH3:25]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 9836155HCID 9836155, compound

Product 1

HCID 59835021HCID 59835021, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

An ice-cold solution of 9-(3-aminobenzyl)-6-(2-furyl)-9H-purine-2-amine (145 mg, 0.48 mmol) in pyridine (3 mL) was treated with acetyl chloride (38 μL, 0.53 mmol), stirred for 1 h, quenched with water, extracted with EtOAc, dried (MgSO4), concentrated in vacuo and purified by chromatography (SiO2: Hexane:EtOAc (1:3) to EtOAc:MeOH (99:1)) to give the title compound (71 mg, 43%) as a yellow solid.

Workup

  1. customquenched with water
  2. extractionextracted with EtOAc
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. custompurified by chromatography (SiO2: Hexane:EtOAc (1:3) to EtOAc:MeOH (99:1))

Sources & evidence

ORD record
ord-abe2e78523c7400081d612fcd86fdcb0
Source dataset
uspto-grants-2008_11
Patent number
US07452894B2

Reaction notes

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