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

HRID 30078

반응식

HRID 30078 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-5a62bd6a3fc94fc19220661b255ffe10
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07423042B2

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