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

HRID 377581Notes

Reaction equation

HRID 377581 reaction equation
C(N(CC)CC)C.[CH2:8]([N:15]1[C:23]([OH:24])=[N:22][C:21]2[C:16]1=[N:17][CH:18]=[N:19][C:20]=2[NH2:25])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.Cl[C:27]([O:29][CH3:30])=[O:28]>C1COCC1>[CH2:8]([N:15]1[C:23]([O:24][C:27]([O:29][CH3:30])=[O:28])=[N:22][C:21]2[C:16]1=[N:17][CH:18]=[N:19][C:20]=2[NH2:25])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 178508651HCID 178508651, compound

Product 1

HCID 120166386-Amino-9-(phenylmethyl)-9H-purin-8-yl methyl carbonateYield 100.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine (202 mg, 2 mmol) and N,N-dimethylaminopyridine (111 mg 0.5 mmol) were added to 9-benzyl-8-hydroxyadenine (241 mg, 1 mmol) dissolved in anhydrous THF (20 ml). After stirring at room temperature for 1 h, methyl chloroformate (113 mg, 1.2 mmol) was added thereto, and the mixture was stirred overnight at room temperature. The resulting reaction mixture was extracted by ethyl acetate (50 ml) and water (50 ml), and the resulting organic layer was concentrated under vacuum followed by addition of ether (20 ml) to obtain the desired compound as crystals (300 mg, Yield: 100%).

Workup

  1. stirringthe mixture was stirred overnight at room temperature
  2. customThe resulting reaction mixture
  3. extractionwas extracted by ethyl acetate (50 ml) and water (50 ml)
  4. concentrationthe resulting organic layer was concentrated under vacuum
  5. additionfollowed by addition of ether (20 ml)

Sources & evidence

ORD record
ord-9a483a77c576492a91792dcca8507f0b
Source dataset
uspto-grants-2000_02
Patent number
US06028076

Reaction notes

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