Water → Methyl [6-(benzyloxy)-9H-purin-9-yl]acetate

HRID 1034602Notes

Reaction equation

HRID 1034602 reaction equation
[CH2:1]([O:8][C:9]1[N:17]=[CH:16][N:15]=[C:14]2[C:10]=1[NH:11][CH:12]=[N:13]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:24][O:25][C:26](=[O:29])[CH2:27]Br.O>CN(C=O)C.C(O)CCC.C(O)(=O)C.O.C(OC(=O)C)C>[CH3:24][O:25][C:26](=[O:29])[CH2:27][N:13]1[CH:12]=[N:11][C:10]2[C:14]1=[N:15][CH:16]=[N:17][C:9]=2[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 8536776-Benzyloxypurine

Product 1

HCID 59289995Methyl [6-(benzyloxy)-9H-purin-9-yl]acetate

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 22056973Butanol acetic acid waterSolvent

Procedure

6-Benzyloxypurine (4.18 g; 18.5 mmol) was added to a suspension of potasiumcarbonate (3.1 g; 22.4 mmol) in DMF (100 ml). After 15 min. bromoacetic acid methyl ester (1.93 ml; 20.4 mmol) was added. The reaction was monitored by TLC in butanol:acetic acid:water 4:1:1. Upon completion, the reaction mixture was portioned between water (600 ml) and ethylacetate (600 ml). The organic phase was dried over magnesium sulphate and evaporated to a volume of ˜10 ml and precipitated with pet. ether. The two products were separated by column chromatography using ethylacetate as the solvent. The products was precipitated in pet. ether. Yield: 2.36 g (43%). Melting point: 111.5-115° C. UV λmax=250 nm (9-alkylated); λmax=260 nm (7-alkylated). 1H-NMR (DMSO-d6): 8.60 (1H, s); 8.43 (1H, s); 7.6-7.35 (5H, m); 5.69 (2H, s); 5.26 (2H, s); 3.75 (3H, s).

Workup

  1. dry with materialThe organic phase was dried over magnesium sulphate
  2. customevaporated to a volume of ˜10 ml
  3. customprecipitated with pet. ether
  4. customThe two products were separated by column chromatography
  5. customThe products was precipitated in pet. ether

Sources & evidence

ORD record
ord-f79edbf0b51b4ab298bee8749f1db8a2
Source dataset
uspto-grants-2013_10
Patent number
US08546309B2

Reaction notes

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