Sodium Carbonate → 4-(4'-Chloro-2'-(methylthio)-4,5'-bipyrimidin-2-ylamino)benzonitrile

HRID 1397177노트

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HRID 1397177 반응식
[CH3:1][S:2][C:3]1[NH:4][C:5](=O)[C:6]([C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]3[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=3)[N:10]=2)=[CH:7][N:8]=1.O=P(Cl)(Cl)[Cl:27].C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[Cl:27][C:5]1[C:6]([C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]3[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=3)[N:10]=2)=[CH:7][N:8]=[C:3]([S:2][CH3:1])[N:4]=1

참가 물질

5

반응물 3

HCID 10340Sodium Carbonate2회HCID 24813Phosphorus oxychlorideHCID 679833184-(4-(2-(Methylthio)-6-oxo-1,6-dihydropyrimidin-5-yl)pyrimidin-2-ylamino)benzonitrile

생성물 1

HCID 867055934-(4'-Chloro-2'-(methylthio)-4,5'-bipyrimidin-2-ylamino)benzonitrile수율 58%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
120 °C

실험 절차

4-(4-(2-(Methylthio)-6-oxo-1,6-dihydropyrimidin-5-yl)pyrimidin-2-ylamino)benzonitrile (34) (700 mg, 2.081 mmol) was dissolved in POCl3 (1940 μl, 20.81 mmol), then the reaction mixture was heated at 120° C. for 3 hours. The reaction mixture was cooled to rt, then was slowly poured into an ice-cooled saturated Na2CO3 solution while stifling vigorously. The reaction mixture was then adjusted to pH 7 with additional Na2CO3 solution. DCM was added to the mixture and the aqueous layer was extracted twice with DCM. The organic extracts were combined, washed with brine, dried over sodium sulfate, then concentrated in vacuo to obtain the desired product as a bright yellow solid (428 mg, 53% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.62 (s, 3 H) 7.39 (d, J=5.05 Hz, 1 H) 7.74 (m, 2 H) 8.00 (m, J=9.09 Hz, 2 H) 8.69-8.80 (m, 1 H) 8.93 (s, 1 H) 10.42 (s, 1 H). MS (ES+): m/z=355.3 (100) [MH+]. HPLC: tR=1.57 minutes over 3 minutes. Purity: 91% [HPLC (LC/MS) at 220 nm].

후처리

  1. temperatureThe reaction mixture was cooled to rt
  2. extractionthe aqueous layer was extracted twice with DCM
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-cce29fea5a074178acda3be3ca86043f
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901147B2

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