Methyl chloroformate → 6-Amino-9-(phenylmethyl)-9H-purin-8-yl methyl carbonate

HRID 842718Notes

Reaction equation

HRID 842718 reaction equation
[CH2:1]([N:8]1[C:16]([OH:17])=[N:15][C:14]2[C:9]1=[N:10][CH:11]=[N:12][C:13]=2[NH2:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.CN(C1C=CC=CN=1)C.Cl[C:36]([O:38][CH3:39])=[O:37]>C1COCC1.O.C(OCC)(=O)C>[CH2:1]([N:8]1[C:16]([O:17][C:36]([O:38][CH3:39])=[O:37])=[N:15][C:14]2[C:9]1=[N:10][CH:11]=[N:12][C:13]=2[NH2:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 178508651HCID 178508651, compound

Product 1

HCID 120166386-Amino-9-(phenylmethyl)-9H-purin-8-yl methyl carbonateYield 100%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

241 mg (1 mmol) of 9-benzyl-8-hydroxyadenine was dissolved in 20 ml of anhydrous THF. To this solution, 202 mg (2 mmol) of triethylamine and 111 mg (0.5 mmol) of dimethylaminopyridine were added and stirred for 1 hr at room temperature. To the resultant mixture, 113 mg (1.2 mmol) of methyl chloroformate was added and stirred overnight at room temperature. 50 ml each of ethyl acetate and water were added thereto for extraction. After the organic layer was removed by vacuum distillation, 20 ml of ether was added to the residue. Then, crystals were collected by filtration (300 mg; yield: 100%).

Workup

  1. stirringstirred overnight at room temperature
  2. extractionfor extraction
  3. customAfter the organic layer was removed by vacuum distillation, 20 ml of ether
  4. additionwas added to the residue
  5. filtrationThen, crystals were collected by filtration (300 mg; yield: 100%)

Sources & evidence

ORD record
ord-5070864dd3a846bf8182963ffb3cae47
Source dataset
uspto-grants-2002_04
Patent number
US06376501B1

Reaction notes

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