Sodium Carbonate → 4-chloro-7-methyl-5-(3-biphenyl)-7H-pyrrolo[2,3-d]pyrimidine

HRID 238030노트

반응식

HRID 238030 반응식
[Cl:1][C:2]1[C:3]2[C:10](I)=[CH:9][N:8]([CH3:12])[C:4]=2[N:5]=[CH:6][N:7]=1.[C:13]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:18]=[CH:17][CH:16]=[C:15](B(O)O)[CH:14]=1.C([O-])([O-])=O.[Na+].[Na+]>C1COCC1.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]>[CH3:12][N:8]1[C:4]2[N:5]=[CH:6][N:7]=[C:2]([Cl:1])[C:3]=2[C:10]([C:17]2[CH:18]=[C:13]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:14]=[CH:15][CH:16]=2)=[CH:9]1

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 2734315(3-Phenylphenyl)boronic acidHCID 426094624-chloro-5-iodo-7-methyl-7H-pyrrolo[2,3-d]pyrimidine

생성물 1

HCID 249051994-chloro-7-methyl-5-(3-biphenyl)-7H-pyrrolo[2,3-d]pyrimidine수율 28%

시약·촉매·용매 2

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 4-chloro-5-iodo-7-methyl-7H-pyrrolo[2,3-d]pyrimidine (10 mg, 0.034 mmol), 3-biphenyl-boronic acid (7.4 mg, 0.038 mmol), Na2CO3 (36.1 mg, 0.34 mmol) and PdCl2(dppf) (1.4 mg, 0.0017 mmol) in THF (10 mL) was heated to reflux overnight under an argon atmosphere. Reaction was concentrated in vacuo and purified by RP-HPLC (MeCN:H2O:0.1% TFA) to yield ZK103 (3 mg, 28% yield). ESI-MS (M+H)+ m/z calcd 320.1, found 320.0.

후처리

  1. temperatureto reflux overnight under an argon atmosphere
  2. customReaction
  3. concentrationwas concentrated in vacuo
  4. custompurified by RP-HPLC (MeCN:H2O:0.1% TFA)

출처 및 근거

ORD 기록
ord-a54222baee56460baf77bb553f690e8b
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642604B2

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