Sodium Carbonate → HCID 71548238、化合物

HRID 595050ノート

反応式

HRID 595050 の反応式
Cl[C:2]1[N:3]=[C:4]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][C@@H:12]2[CH3:17])[C:5]2[CH2:10][S:9][CH2:8][C:6]=2[N:7]=1.[CH:18]1([NH:21][C:22]([NH:24][C:25]2[CH:30]=[CH:29][C:28](B3OC(C)(C)C(C)(C)O3)=[CH:27][CH:26]=2)=[O:23])[CH2:20][CH2:19]1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH:18]1([NH:21][C:22]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([C:2]3[N:3]=[C:4]([N:11]4[CH2:16][CH2:15][O:14][CH2:13][C@@H:12]4[CH3:17])[C:5]4[CH2:10][S:9][CH2:8][C:6]=4[N:7]=3)=[CH:27][CH:26]=2)=[O:23])[CH2:20][CH2:19]1

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 44119149N-Cyclopropyl-N'-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ureaHCID 89487530HCID 89487530、化合物

生成物 1

HCID 71548238HCID 71548238、化合物

試薬・触媒・溶媒 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 18180031Water 1,2-dimethoxyethane溶媒

反応条件

温度
70 °C

実験手順

To a solution of 2-chloro-5,7-dihydro-4-((S)-3-methylmorpholino)thieno[3,4-d]pyrimidine (100 mg, 0.37 mmol) in DME/H2O (4:1, 10 mL) was added 1-cyclopropyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea (124 mg, 0.41 mmol), and Na2CO3 (118 mg, 1.11 mmol) followed by addition of PdCl2(dppf) (15 mg, 0.02 mmol). The resulting mixture was heated to 70° C. and stirred overnight under nitrogen. The solvent was removed under reduced pressure to give a residue which was partitioned between ethyl acetate and water. The organic layer was washed with brine dried (Na2SO4) and concentrated to give a crude product which was purified by preparative TLC (DCM/MeOH=20/1) to give the desired product, as a yellow solid (20 mg, 13%).

後処理

  1. customThe solvent was removed under reduced pressure
  2. customto give a residue which
  3. customwas partitioned between ethyl acetate and water
  4. washThe organic layer was washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customto give a crude product which
  8. customwas purified by preparative TLC (DCM/MeOH=20/1)

出典と根拠

ORDレコード
ord-27972c7b655c4253beb36f0f2e4230ad
出典データセット
uspto-grants-2016_01
特許番号
US09242993B2

反応ノート

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