Methyl iodide → Methyl 2,4-dichloro-6-(m-tolylamino)pyrimidine-5-carboxylate

HRID 2092735ノート

反応式

HRID 2092735 の反応式
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([C:9]([OH:11])=[O:10])=[C:4]([NH:12][C:13]2[CH:14]=[C:15]([CH3:19])[CH:16]=[CH:17][CH:18]=2)[N:3]=1.[C:20]([O-])(O)=O.[Na+].IC>CN(C=O)C>[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([C:9]([O:11][CH3:20])=[O:10])=[C:4]([NH:12][C:13]2[CH:14]=[C:15]([CH3:19])[CH:16]=[CH:17][CH:18]=2)[N:3]=1

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 516892Sodium Bicarbonate2 回HCID 583175932,4-Dichloro-6-(m-tolylamino)pyrimidine-5-carboxylic acid

生成物 1

HCID 58317610Methyl 2,4-dichloro-6-(m-tolylamino)pyrimidine-5-carboxylate収率 65.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 2,4-dichloro-6-(m-tolylamino)pyrimidine-5-carboxylic acid (7.67 g, 25.7 mmol) in DMF (80 mL) was added NaHCO3 (3.30 g, 39.3 mmol) and iodomethane (1.605 mL, 25.7 mmol) at 0° C. The mixture was stirred at RT for 14 h, after which saturated aq NaHCO3 was added. The mixture was extracted with EtOAc. The organic layers were washed with aqueous NaHOC3, water, and brine, were dried over anhydrous Na2SO4, and then filtered through SiO2. The filtrate was concentrated under reduced pressure. The residue was triturated with isopropyl ether and filtered to give a first batch (5.28 g) of the title compound. The filtrate was concentrated, triturated with IPE, and filtered to give a second batch (0.66 g) of the title compound as a yellow solid (total 5.94 g, 74%). 1H NMR (500 MHz, CDCl3) δ ppm 2.38 (s, 3H), 4.00 (s, 3H), 7.02-7.03 (m, 1H), 7.27-7.33 (m, 2H), 7.44-7.46 (m, 1H), 10.30 (br s, 1H). [M+H] calc'd for C13H12Cl2N3O2, 312. found, 312.

後処理

  1. extractionThe mixture was extracted with EtOAc
  2. washThe organic layers were washed with aqueous NaHOC3, water, and brine
  3. dry with materialwere dried over anhydrous Na2SO4
  4. filtrationfiltered through SiO2
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customThe residue was triturated with isopropyl ether
  7. filtrationfiltered

出典と根拠

ORDレコード
ord-8d139738846c416aaf7d021bceb77ae7
出典データセット
uspto-grants-2013_05
特許番号
US08440689B2

反応ノート

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