Potassium Phosphate, Tribasic → 2-(3-Hydroxyphenyl)-9-(2-methoxyphenyl)-9H-purine-6-carboxamide

HRID 2427956노트

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HRID 2427956 반응식
[NH2:1][C:2]1[C:3]([C:24]([O:26]CC)=O)=[N:4][C:5]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([OH:23])[CH:18]=2)=[N:6][C:7]=1[NH:8][C:9]1C=CC=CC=1OC.[NH2:29]C1C(C(OCC)=O)=NC(Cl)=NC=1NC1C=CC=CC=1OC.OC1C=C(B(O)O)C=CC=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2C=CC=CC=2[C:82]2[C:87]([O:88][CH3:89])=[CH:86][CH:85]=[CH:84][C:83]=2OC)CCCCC1>O1CCCC1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[OH:23][C:19]1[CH:18]=[C:17]([C:5]2[N:6]=[C:7]3[C:2]([N:1]=[CH:9][N:8]3[C:82]3[CH:83]=[CH:84][CH:85]=[CH:86][C:87]=3[O:88][CH3:89])=[C:3]([C:24]([NH2:29])=[O:26])[N:4]=2)[CH:22]=[CH:21][CH:20]=1

참가 물질

9

반응물 5

HCID 62657Potassium Phosphate, TribasicHCID 2734359(3-hydroxyphenyl)boronic AcidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 57474574Ethyl 5-amino-2-(3-hydroxyphenyl)-6-(2-methoxyphenylamino)pyrimidine-4-carboxylateHCID 57474575Ethyl 5-amino-2-chloro-6-(2-methoxyphenylamino)pyrimidine-4-carboxylate

생성물 1

HCID 574745682-(3-Hydroxyphenyl)-9-(2-methoxyphenyl)-9H-purine-6-carboxamide수율 12%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

Ethyl 5-amino-2-(3-hydroxyphenyl)-6-(2-methoxyphenylamino)pyrimidine-4-carboxylate. In a microwave flask was placed ethyl 5-amino-2-chloro-6-(2-methoxyphenylamino)pyrimidine-4-carboxylate (404 mg, 1.252 mmol), 3-hydroxyphenylboronic acid (259 mg, 1.878 mmol), potassium phosphate (531 mg, 2.504 mmol), dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (77 mg, 0.188 mmol) and palladium (II) acetate (42.2 mg, 0.188 mmol) in tetrahydrofuran (20 mL) and water (2 mL) and the reaction mixture was heated at 120° C. for 20 min in the microwave. The reaction mixture was filtered and the solvent was removed under reduced pressure. The crude material was purified by column chromatography (SiO2, 80-60% n-hexanes in ethyl acetate) and semi prep HPLC (20-100% acetonitrile+0.1% TFA in H2O+0.1% TFA, over 30 min). Fractions containing product were neutralized with potassium carbonate (saturated aqueous solution), extracted with ethyl acetate and dried over magnesium sulfate to provide the title compound (57.8 mg, 0.152 mmol, 12% yield). MS (ESI) m/z 381.4 [M+1]+.

후처리

  1. customIn a microwave flask was placed
  2. filtrationThe reaction mixture was filtered
  3. customthe solvent was removed under reduced pressure
  4. customThe crude material was purified by column chromatography (SiO2, 80-60% n-hexanes in ethyl acetate) and semi prep HPLC (20-100% acetonitrile+0.1% TFA in H2O+0.1% TFA, over 30 min)
  5. additionFractions containing product
  6. extractionextracted with ethyl acetate
  7. dry with materialdried over magnesium sulfate

출처 및 근거

ORD 기록
ord-7ea2bf5b7628417ea8649938874b95e4
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07968556B2

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