Sodium Acetate → HCID 57500644、化合物

HRID 604356ノート

反応式

HRID 604356 の反応式
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

参加物

5

反応物 3

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

生成物 1

HCID 57500644HCID 57500644、化合物収率 79.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
120 °C

実験手順

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+l]+, 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.

後処理

  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

出典と根拠

ORDレコード
ord-5b27198be77b46d88b08548eabb3428a
出典データセット
uspto-grants-2011_03
特許番号
US07910600B2

反応ノート

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