Sodium Acetate → Methyl 3-(methylthio)-5-oxo-5,6-dihydropyrimido[4,5-c]quinoline-8-carboxylate

HRID 2420943노트

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HRID 2420943 반응식
Br[C:2]1[C:3]([C:10]([O:12]C)=O)=[N:4][C:5]([S:8][CH3:9])=[N:6][CH:7]=1.Cl.[NH2:15][C:16]1[CH:21]=[C:20]([C:22]([O:24][CH3:25])=[O:23])[CH:19]=[CH:18][C:17]=1B(O)O.C([O-])(=O)C.[Na+]>CN(C=O)C>[CH3:9][S:8][C:5]1[N:6]=[CH:7][C:2]2[C:17]3[CH:18]=[CH:19][C:20]([C:22]([O:24][CH3:25])=[O:23])=[CH:21][C:16]=3[NH:15][C:10](=[O:12])[C:3]=2[N:4]=1

참가 물질

5

반응물 3

HCID 517045Sodium AcetateHCID 2794729Methyl 5-bromo-2-(methylsulfanyl)pyrimidine-4-carboxylateHCID 16427083[2-Amino-4-(methoxycarbonyl)phenyl]boronic acid--hydrogen chloride (1/1)

생성물 1

HCID 57500644Methyl 3-(methylthio)-5-oxo-5,6-dihydropyrimido[4,5-c]quinoline-8-carboxylate수율 79.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
120 °C

실험 절차

In a microwave vessel, methyl 5-bromo-2-(methylthio)pyrimidine-4-carboxylate (1.0 eq, 274 mg, 1.18 mmol), 2-amino-4-(methoxycarbonyl)phenylboronic acid hydrochloride (1.2 eq, 329 mg, 1.42 mmol), and sodium acetate (3.0 eq, 291 mg, 3.55 mmol) were mixed in anhydrous DMF (2 ml). The mixture was degassed by bubbling nitrogen gas in the solution for 10 min and the reaction heated under microwaves at 120° C. for 30 min. After cooling down the expected material crashed out of NMP. The solid was filtered, suspended in water filtered and dried. The material was triturated in AcOEt and filtered give a yellow solid. The same procedure was repeated 9 times using the same amounts of materials to provide methyl 3-(methylthio)-5-oxo-5,6-dihydropyrimido[4,5-c]quinoline-8-carboxylate (283 mg, 10% yield). LCMS (ES): >95% pure, m/z 302 [M+1]+, 1H NMR (DMSO-d6, 400 MHz) δ 2.71 (s, 3H), 3.89 (s, 3H), 7.80 (dd, J=1.6, J=8.4, 1H), 7.97 (d, J=1.6, 1H), 8.59 (d, J=8.8, 1H), 9.98 (s, 1H), 12.34 (s, 1H) ppm.

후처리

  1. customThe mixture was degassed
  2. customby bubbling nitrogen gas in the solution for 10 min
  3. temperatureAfter cooling down the expected material
  4. filtrationThe solid was filtered
  5. filtrationfiltered
  6. customdried
  7. customThe material was triturated in AcOEt
  8. filtrationfiltered
  9. customgive a yellow solid

출처 및 근거

ORD 기록
ord-0ced889c29104089be6c7460f130d288
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07956064B2

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