Potassium Carbonate → 5-phenyl-6-(4-(2-(pyrrolidin-1-yl)ethoxy)phenyl)furo[2,3-d]pyrimidin-4 (3H)-one

HRID 502639ノート

反応式

HRID 502639 の反応式
I[C:2]1[O:11][C:5]2[N:6]=[CH:7][NH:8][C:9](=[O:10])[C:4]=2[C:3]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CC1(C)C(C)(C)OB([C:26]2[CH:39]=[CH:38][C:29]([O:30][CH2:31][CH2:32][N:33]3[CH2:37][CH2:36][CH2:35][CH2:34]3)=[CH:28][CH:27]=2)O1.C([O-])([O-])=O.[K+].[K+]>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]>[C:12]1([C:3]2[C:4]3[C:9](=[O:10])[NH:8][CH:7]=[N:6][C:5]=3[O:11][C:2]=2[C:26]2[CH:27]=[CH:28][C:29]([O:30][CH2:31][CH2:32][N:33]3[CH2:34][CH2:35][CH2:36][CH2:37]3)=[CH:38][CH:39]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 567768331-(2-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)ethyl)pyrrolidineHCID 586032796-iodo-5-phenyl-3H-furo[2,3-d]pyrimidin-4-one

生成物 1

HCID 586032805-phenyl-6-(4-(2-(pyrrolidin-1-yl)ethoxy)phenyl)furo[2,3-d]pyrimidin-4 (3H)-one

試薬・触媒・溶媒 1

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

反応条件

温度
80 °C

実験手順

Compound 11 (242 mg, 0.716 mmol), 1-(2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)ethyl)pyrrolidine 25 [prepared by Specific Method A2] (500 mg, 1.58 mmol), K2CO3 (247 mg, 1.79 mmol), and Pd(dppf)2Cl2 (524 mg, 0.072 mmol) were combined in a pyrex tube. After purging with N2, DMF (7.3 mL) and H2O (1.45 mL) were added and the tube was sealed. The mixture was heated at 80° C. for 5 h. After cooling to RT, CH2Cl2 was added and the organic layers were washed with H2O, followed by brine. The organic layers were then dried over Na2SO4 and concentrated to a brown oil. Flash chromatography (SiO2, gradient eluent: 0-15% MeOH in CH2Cl2), followed by trituration with EtOAc and filtration afforded compound 26.

後処理

  1. customAfter purging with N2, DMF (7.3 mL) and H2O (1.45 mL)
  2. additionwere added
  3. customthe tube was sealed
  4. temperatureAfter cooling to RT
  5. additionCH2Cl2 was added
  6. washthe organic layers were washed with H2O
  7. dry with materialThe organic layers were then dried over Na2SO4
  8. concentrationconcentrated to a brown oil
  9. filtrationFlash chromatography (SiO2, gradient eluent: 0-15% MeOH in CH2Cl2), followed by trituration with EtOAc and filtration

出典と根拠

ORDレコード
ord-445d734ccabb4481bd78e1754dc526e3
出典データセット
uspto-grants-2010_08
特許番号
US07776867B2

反応ノート

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