Sodium Carbonate → 1-Methyl-7-(pivaloyloxymethyl)xanthine

HRID 263098

반응식

HRID 263098 반응식
[CH3:1][N:2]1[C:11](=[O:12])[C:10]2[NH:9][CH:8]=[N:7][C:6]=2[NH:5][C:3]1=[O:4].[C:13](=O)([O-])[O-].[Na+].[Na+].ClC[CH2:21][C:22]([CH3:27])([CH3:26])[C:23]([O-:25])=[O:24]>CN(C=O)C>[CH3:1][N:2]1[C:11](=[O:12])[C:10]2[N:9]([CH2:13][O:25][C:23](=[O:24])[C:22]([CH3:27])([CH3:26])[CH3:21])[CH:8]=[N:7][C:6]=2[NH:5][C:3]1=[O:4]

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 802201-MethylxanthineHCID 217530474-Chloro-2,2-dimethylbutanoate

생성물 1

HCID 128798411-Methyl-7-(pivaloyloxymethyl)xanthine수율 25.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

To a mixture of 1-methylxanthine (844 mg, 5.08 mmoles) and sodium carbonate (538 mg, 5.08 mmoles) in 20 ml of dry DMF under nitrogen was slowly added over a period of 1 hour a solution of chloromethylpivalate (828 μl, 5.59 mmole) in 6 ml DMF at room temperature and the reaction mixture stirred overnight. The mixture was filtered, the filtrate evaporated to dryness and the residue triturated with 50 ml of 10 vol. %. EtOH/CHCl3. The solids obtained were starting material and the organic phase was chromatographed (10 vol. % EtOH/CHCl3) on silica gel plates. Two products were observed by eluting with 125 ml of 10 vol. % EtOH/CHCl3 and the band Rf, 0.48 obtained as 365 mg of the desired product. The other band proved to be the 3,7-disubstituted material.

후처리

  1. filtrationThe mixture was filtered
  2. customthe filtrate evaporated to dryness
  3. customthe residue triturated with 50 ml of 10 vol. %
  4. customThe solids obtained
  5. customthe organic phase was chromatographed (10 vol. % EtOH/CHCl3) on silica gel plates
  6. washby eluting with 125 ml of 10 vol. % EtOH/CHCl3

출처 및 근거

ORD 기록
ord-1fbdc658c03648f1b9e6d51e8ac9fe6d
출처 데이터셋
uspto-grants-1979_05
특허 번호
US04156081

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