Water → N-[3-(2-chloro-5-methyl-5H-pyrrolo[3,2-d]pyrimidin-7-yl)phenyl]methanesulfonamide

HRID 1803910ノート

反応式

HRID 1803910 の反応式
[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[N:10]([CH3:11])[CH:9]=[C:8](I)[C:6]=2[N:7]=1.[CH3:13][S:14]([NH:17][C:18]1[CH:19]=[C:20](B(O)O)[CH:21]=[CH:22][CH:23]=1)(=[O:16])=[O:15].C([O-])([O-])=O.[Na+].[Na+].O>CN(C=O)C>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[N:10]([CH3:11])[CH:9]=[C:8]([C:22]3[CH:23]=[C:18]([NH:17][S:14]([CH3:13])(=[O:15])=[O:16])[CH:19]=[CH:20][CH:21]=3)[C:6]=2[N:7]=1

参加物

6

反応物 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 27735353-Methylsulfonylaminophenylboronic acidHCID 713077402-Chloro-7-iodo-5-methyl-5H-pyrrolo[3,2-d]pyrimidine

生成物 1

HCID 86652564N-[3-(2-chloro-5-methyl-5H-pyrrolo[3,2-d]pyrimidin-7-yl)phenyl]methanesulfonamide収率 68%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

To a solution of 2-chloro-7-iodo-5-methyl-5H-pyrrolo[3,2-d]pyrimidine (0.140 g, 0.48 mmol, 1.0 eq.) in DMF (6 ml) was added 3-methanesulfonylaminophenylboronic acid (0.124 g, 0.576 mmol, 1.2 eq.) followed by aqueous Na2CO3 (2M, 0.7 ml, 1.44 mmol, 3.0 eq.). A flow of nitrogen was bubbled through the mixture during 15 to 20 min before adding Pd[PPh3]4 (0.055 g, 0.048 mmol, 0.1 eq.). The mixture was then heated up to 100° C. overnight. After cooling down the reaction mixture to room temperature a large amount of water (around 60 ml) was added and the mixture extracted with ethyl acetate (3 times). After evaporation the residue was purified by column chromatography using petroleum spirit/ethyl acetate (1:4) as eluent. The product was obtained as a pale yellow solid (110 mg, 68%). LRMS (EI): m/z calcd for [M+H]+ 337.05 found 337.2.

後処理

  1. customA flow of nitrogen was bubbled through the mixture during 15 to 20 min
  2. additionwas added
  3. extractionthe mixture extracted with ethyl acetate (3 times)
  4. customAfter evaporation the residue
  5. customwas purified by column chromatography

出典と根拠

ORDレコード
ord-fb045032770243aeb5e0c005b52fa4c8
出典データセット
uspto-grants-2013_01
特許番号
US08354408B2

反応ノート

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