Sodium Carbonate → HCID 71286171、化合物

HRID 1752445ノート

反応式

HRID 1752445 の反応式
CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]3[CH:21]=[CH:20][C:19]([O:22][C:23]([F:26])([F:25])[F:24])=[CH:18][CH:17]=3)=[CH:11][CH:10]=2)O1.[NH2:28][C:29](=[O:43])[C@@H:30]([NH:32][C:33]1[N:38]=[C:37](Cl)[N:36]=[C:35]([C:40]([NH2:42])=[O:41])[CH:34]=1)[CH3:31].C([O-])([O-])=O.[Na+].[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCOCC1>[NH2:28][C:29](=[O:43])[C@@H:30]([NH:32][C:33]1[N:38]=[C:37]([C:9]2[CH:10]=[CH:11][C:12]([O:15][C:16]3[CH:17]=[CH:18][C:19]([O:22][C:23]([F:24])([F:25])[F:26])=[CH:20][CH:21]=3)=[CH:13][CH:14]=2)[N:36]=[C:35]([C:40]([NH2:42])=[O:41])[CH:34]=1)[CH3:31]

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 712858874,4,5,5-Tetramethyl-2-[4-[4-(trifluoromethoxy)phenoxy]phenyl]-1,3,2-dioxaborolaneHCID 89422280HCID 89422280、化合物

生成物 1

HCID 71286171HCID 71286171、化合物収率 31.3%

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
10 °C

実験手順

A 50-mL vial with a screw-top septum was charged with 200 mg of 4,4,5,5-tetramethyl-2-(4-(4-(trifluoromethoxy)phenoxy)phenyl)-1,3,2-dioxaborolane, 1 equivalent (S)-6-((1-amino-1-oxopropan-2-yl)amino)-2-chloropyrimidine-4-carboxamide (129 mg, 0.53 mmol), 1.5 mL 2M aqueous Na2CO3, 0.07 equivalents PdCl2(PPh3)2 (28 mg, 0.04 mmol), and 8 mL dioxane. The vial was purged with nitrogen and heated to 10° C. for 6 h, at which time the reaction was complete. The mixture was diluted with 100 mL EtOAc and washed two times with 100 mL water. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was chromatographed by combiflash using a 40-gram silica column with a gradient EtOAc (100% max) in hexane to provide 76 mg (31% yield) of (S)-6-((1-amino-1-oxopropan-2-yl)amino)-2-(4-(4-(trifluoromethoxy)phenoxy)phenyl)pyrimidine-4-carboxamide as a white solid. m/z 461, 1H NMR (CD3OD): 8.56-8.49 (m, 2H), 7.35-7.27 (m, 2H), 7.17-7.11 (m, 3H), 7.09-7.02 (m, 2H), 4.64-4.49 (m, 1H), 4.56-1.49 (m, 3H).

後処理

  1. customThe vial was purged with nitrogen
  2. additionThe mixture was diluted with 100 mL EtOAc
  3. washwashed two times with 100 mL water
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was chromatographed by combiflash

出典と根拠

ORDレコード
ord-ce7006f5c7a14541929ab3b8310aa74a
出典データセット
uspto-grants-2015_10
特許番号
US09163008B2

反応ノート

読み込み中…