Sodium Carbonate → HCID 71548327、化合物

HRID 595052ノート

反応式

HRID 595052 の反応式
Cl[C:2]1[N:3]=[C:4]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][C@@H:14]2[CH3:19])[C:5]2[CH2:10][S:9](=[O:12])(=[O:11])[CH2:8][C:6]=2[N:7]=1.[CH:20]1([NH:23][C:24]([NH:26][C:27]2[CH:32]=[CH:31][C:30](B3OC(C)(C)C(C)(C)O3)=[CH:29][CH:28]=2)=[O:25])[CH2:22][CH2:21]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:20]1([NH:23][C:24]([NH:26][C:27]2[CH:32]=[CH:31][C:30]([C:2]3[N:3]=[C:4]([N:13]4[CH2:18][CH2:17][O:16][CH2:15][C@@H:14]4[CH3:19])[C:5]4[CH2:10][S:9](=[O:12])(=[O:11])[CH2:8][C:6]=4[N:7]=3)=[CH:29][CH:28]=2)=[O:25])[CH2:22][CH2:21]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 894946042-chloro-5,7-dihydro-4-((S)-3-methylmorpholino)thieno[3,4-d]pyrimidine 6,6-dioxide

生成物 1

HCID 71548327HCID 71548327、化合物収率 11%

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 6,6-dioxide (96 mg, 0.32 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 (106 mg, 0.35 mmol), and Na2CO3 (102 mg, 0.96 mmol) followed by 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 vacuum to give a residue which was partitioned between ethyl acetate and water. The organic layer was separated, dried (Na2SO4) and the solvent removed to give crude product which was purified by preparative TLC (DCM/MeOH=20/1) to give the desired product as a yellow solid (15 mg, 11%).

後処理

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

出典と根拠

ORDレコード
ord-3d2677fad1a34b28ac2d9aa683f2b1ee
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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