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

HRID 502639노트

반응식

HRID 502639 반응식
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

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

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

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온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-445d734ccabb4481bd78e1754dc526e3
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07776867B2

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