Tetrahydrofuran → 4-(3-(2,6-dimethylphenylamino)-6-(phenylamino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)butan-2-ol

HRID 2357987Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2357987
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[NH:9][C:10]1[C:18]2[C:13](=[N:14][C:15]([NH:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[N:16][CH:17]=2)[N:12]([CH2:26][CH2:27][CH:28]2[CH2:30][O:29]2)[N:11]=1.C1COCC1.CC([BH-](C(C)C(C)C)C(C)C(C)C)C(C)C.[Li+]>C(Cl)Cl>[CH3:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[C:3]=1[NH:9][C:10]1[C:18]2[C:13](=[N:14][C:15]([NH:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)=[N:16][CH:17]=2)[N:12]([CH2:26][CH2:27][CH:28]([OH:29])[CH3:30])[N:11]=1

Komponenten

5

Edukt 3

HCID 8028TetrahydrofuranHCID 5060263Lithium hydridotris(3-methylbutan-2-yl)borate(1-)HCID 58836882N3-(2,6-dimethylphenyl)-1-(2-(oxiran-2-yl)ethyl)-N6-phenyl-1H-pyrazolo[3,4-d]pyrimidine-3,6-diamine

Produkt 1

HCID 160489004-(3-(2,6-dimethylphenylamino)-6-(phenylamino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)butan-2-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 9 mg (0.02 mmol) of N3-(2,6-dimethylphenyl)-1-(2-(oxiran-2-yl)ethyl)-N6-phenyl-1H-pyrazolo[3,4-d]pyrimidine-3,6-diamine 42 (Example 9, Step A) in 2.5 mL of CH2Cl2 was cooled to 0° C. and treated with 120 μl (1.0 M, 0.12 mmol) of a THF solution of LS-Selectride. The resulting tan solution was stirred at 0° C. for 1.25 h. The reaction mixture was quenched with saturated aqueous sodium potassium tartrate (8 mL) and stirred vigorously at room temperature overnight. The mixture was extracted with CH2Cl2 (10 mL), and the organic layer was dried over Na2SO4 and filtered. The filtrate was purified by chromatography on silica gel (eleuens CH2Cl2:MeOH, 98:2) to give the title compound 46. 1H-NMR (CD3OD) δ 1.16 (d, J=6.3 Hz, 3H), 1.80-1.99 (m, 2H), 2.26 (s, 6H), 3.64-3.72 (m, 1H), 4.13-4.23 (m, 2H), 7.00 (t, J=7.4 Hz, 1H), 7.10-7.17 (m, 3H), 7.30 (t, J=8.0 Hz, 2H), 7.75 (d, J=7.7 Hz, 2H), 8.08 (s, 1H). Mass Spectrum (ESI) m/e=403.1 (M+1).

Aufarbeitung

  1. customThe reaction mixture was quenched with saturated aqueous sodium potassium tartrate (8 mL)
  2. stirringstirred vigorously at room temperature overnight
  3. extractionThe mixture was extracted with CH2Cl2 (10 mL)
  4. dry with materialthe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. customThe filtrate was purified by chromatography on silica gel (eleuens CH2Cl2:MeOH, 98:2)

Quellen und Nachweise

ORD-Eintrag
ord-1bfcbde0813f43eab06d563b7fe25e6c
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07763624B2

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