Water → 4-Chloro-6-((2,6-difluorophenyl)amino)-2-(methylthio)pyrimidine-5-carbaldehyde

HRID 30078

反応式

HRID 30078 の反応式
Cl[C:2]1[C:7]([CH:8]=[O:9])=[C:6]([Cl:10])[N:5]=[C:4]([S:11][CH3:12])[N:3]=1.[F:13][C:14]1[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[C:15]=1[NH2:16].CCN(CC)CC.O>C(Cl)(Cl)Cl>[Cl:10][C:6]1[C:7]([CH:8]=[O:9])=[C:2]([NH:16][C:15]2[C:14]([F:13])=[CH:20][CH:19]=[CH:18][C:17]=2[F:21])[N:3]=[C:4]([S:11][CH3:12])[N:5]=1

参加物

6

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 796472,6-DifluoroanilineHCID 46140044,6-Dichloro-2-(methylsulfanyl)pyrimidine-5-carbaldehyde

生成物 1

HCID 99447374-Chloro-6-((2,6-difluorophenyl)amino)-2-(methylthio)pyrimidine-5-carbaldehyde収率 76.2%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

To a solution of 4,6-dichloro-2-methylsulfanyl-pyrimidine-5-carbaldehyde (11.1 grams(hereinafter “g”), 50 millimoles (hereinafter “mmol”)) in CHCl3 (100 milliliters (hereinafter “mL”)) was added 2,6-difluoroaniline (8.07 mL, 75 mmol, 1.5 equivalents (hereinafter “eq”)) followed by Et3N (10.43 mL, 75 mmol, 1.5 eq). The reaction mixture turned yellow and was heated to reflux for 24 h, H2O (50 mL) was added and the layers were separated. The organic layer was evaporated and the crude product was recrystallized from 200 mL of a methanol: H2O mixture (2:1) to give 12.03 g (76%) of pure 4-chloro-6-(2,6-difluoro-phenylamino)-2-methylsulfanyl-pyrimidine-5-carbaldehyde. 1H-NMR: δ 2.21 (s, 3H), 6.91 (m, 2H), 7.24 (m, 1H), 10.29 (s, 1H), 10.35 (br s, 1H). LC MS (m/e)=316 (MH+).

後処理

  1. temperaturewas heated
  2. temperatureto reflux for 24 h
  3. customthe layers were separated
  4. customThe organic layer was evaporated
  5. customthe crude product was recrystallized from 200 mL of a methanol

出典と根拠

ORDレコード
ord-5a62bd6a3fc94fc19220661b255ffe10
出典データセット
uspto-grants-2008_09
特許番号
US07423042B2

関連ノート

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