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

HRID 44424

反応式

HRID 44424 の反応式
[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](Cl)(=[O:17])[C:14](Cl)=O.CN(C=O)C.[CH3:24][NH:25][C:26]1[CH:31]=[CH:30][C:29]([CH:32]([CH3:34])[CH3:33])=[CH:28][CH:27]=1>C(Cl)(Cl)Cl.CC#N>[CH:32]([C:29]1[CH:30]=[CH:31][C:26]([N:25]([CH3:24])[C:13](=[O:17])[CH2:14][N:9]2[C:10]3[C:11](=[O:12])[N:2]([CH3:1])[C:3](=[O:4])[NH:5][C:6]=3[N:7]=[CH:8]2)=[CH:27][CH:28]=1)([CH3:34])[CH3:33]

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 802201-MethylxanthineHCID 138880Aniline, p-isopropyl-N-methyl-

生成物 1

HCID 59205107N-(4-isopropylphenyl)-N-methyl-2-(1-methyl-2,6-dioxo-1,2,3,6-tetrahydropurin-7-yl)acetamide収率 51%

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 120 (0.25 g, 1.11 mmol) in CHCl3 (20 mL) and CH3CN (20 mL) at 0° C. was added oxalyl chloride (0.84 g, 6.69 mmol) and a catalytic amount of DMF. The resulting solution was stirred for 2 h at rt and concentrated in vacuo. The residue was re-dissolved in CHCl3 and the resulting solution cooled to 0° C. To this mixture was added N-methyl-4-isopropyl aniline (0.29 g, 2 mmol) and the reaction was stirred overnight warming to rt. The reaction was then 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 and the product was purified by chromatography on silica gel eluting with EtOAc/hexanes and EtOAc/MeOH to yield 392 (0.2 g, 51%) as a light brown solid. mp: 271-273° C. MS (APCI): m/z 356.2 [H+H]+ Anal. Calcd. For C18H21N5O3. 0.35 H2O: C, 59.77; H, 6.05; N, 19.36. Found C, 59.77; H, 6.07; N, 19.29.

後処理

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was re-dissolved in CHCl3
  3. temperaturethe resulting solution cooled 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-ea94e74472e04b1db751cf9295bd9520
出典データセット
uspto-grants-2013_09
特許番号
US08541423B2

関連ノート

読み込み中…