Dimethylformamide → 2-(1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydropurin-7-yl)-N-(4-isopropylphenyl)-N-methylacetamide

HRID 1924358

反応式

HRID 1924358 の反応式
[N:1]1([C:12](=[O:13])[C:11]2[N:10]([CH2:14][C:15]([OH:17])=O)[CH:9]=[N:8][C:7]=2[N:5]([CH3:6])[C:3]1=[O:4])[CH3:2].C(Cl)(=O)C(Cl)=O.CN(C=O)C.[CH3:29][NH:30][C:31]1[CH:36]=[CH:35][C:34]([CH:37]([CH3:39])[CH3:38])=[CH:33][CH:32]=1>C(Cl)(Cl)Cl.CC#N>[CH3:2][N:1]1[C:12](=[O:13])[C:11]2[N:10]([CH2:14][C:15]([N:30]([C:31]3[CH:36]=[CH:35][C:34]([CH:37]([CH3:39])[CH3:38])=[CH:33][CH:32]=3)[CH3:29])=[O:17])[CH:9]=[N:8][C:7]=2[N:5]([CH3:6])[C:3]1=[O:4]

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 69550AcefyllineHCID 138880Aniline, p-isopropyl-N-methyl-

生成物 1

HCID 592051082-(1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydropurin-7-yl)-N-(4-isopropylphenyl)-N-methylacetamide収率 84.4%

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒2 回HCID 6342Acetonitrile溶媒

実験手順

To a solution of acid 101 (0.5 g, 2.1 mmol) in CHCl3 (30 mL) and CH3CN (30 mL) at 0° C. was added oxalyl chloride (1.59 g, 12.6 mmol) and a catalytic amount of DMF. The resulting solution was stirred for 2 h at rt and concentrated in vacuo. The resulting residue was re-dissolved in CHCl3 and cooled to 0° C. To this mixture was added N-methyl-4-isopropyl aniline (0.78 g, 5.2 mmol) and the reaction was stirred overnight warming to rt. The reaction mixture was diluted with CHCl3 (30 mL) and washed with 1 N HCl (50 mL). The combined organic layers were washed with water (75 mL), dried over Na2SO4 and concentrated in vacuo. The product was purified by chromatography on silica gel eluting with EtOAc/hexanes and EtOAc/MeOH to yield 393 as a light yellow solid (0.65 g, 84.4%). mp: 231-233° C. MS (APCI): m/z 370.2 [M+H]+. Anal. Calcd. For C19H23N5O3.0.1H2O: C, 61.47; H, 6.30; N, 18.87. Found C, 61.28; H, 6.19; N, 18.57.

後処理

  1. concentrationconcentrated in vacuo
  2. dissolutionThe resulting residue was re-dissolved in CHCl3
  3. temperaturecooled to 0° C
  4. stirringthe reaction was stirred overnight
  5. temperaturewarming to rt
  6. washwashed with 1 N HCl (50 mL)
  7. washThe combined organic layers were washed with water (75 mL)
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated in vacuo
  10. customThe product was purified by chromatography on silica gel eluting with EtOAc/hexanes and EtOAc/MeOH

出典と根拠

ORDレコード
ord-a2ec888260af4a1080c4046afdeb4a24
出典データセット
uspto-grants-2012_05
特許番号
US08178542B2

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