t-Butanol tetrahydrofuran water → (S)-4-(2-amino-4-chloro-7-((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)but-3-yne-1,2-diol

HRID 1984113

Reaktionsgleichung

Reaktionsgleichung von HRID 1984113
[C:1]([C:5]1[C:13]2[C:12]([Cl:14])=[N:11][C:10]([NH2:15])=[N:9][C:8]=2[N:7]([CH2:16][C:17]2[C:22]([CH3:23])=[C:21]([O:24][CH3:25])[C:20]([CH3:26])=[CH:19][N:18]=2)[CH:6]=1)#CC=C.CC[C@H]1[C@H]2C[C@H]([C@H](OC3C4C(=CC=CC=4)C(O[C@H](C4C=CN=C5C=4C=C(OC)C=C5)[C@@H]4N5C[C@H](CC)[C@@H](CC5)C4)=NN=3)C3C=CN=C4C=3C=C([O:48]C)C=C4)N(CC2)C1.C[C:86]([OH:89])([CH3:88])[CH3:87].C1COCC1.O>>[NH2:15][C:10]1[N:11]=[C:12]([Cl:14])[C:13]2[C:5]([C:1]#[C:87][C@H:86]([OH:89])[CH2:88][OH:48])=[CH:6][N:7]([CH2:16][C:17]3[C:22]([CH3:23])=[C:21]([O:24][CH3:25])[C:20]([CH3:26])=[CH:19][N:18]=3)[C:8]=2[N:9]=1

Komponenten

4

Edukt 3

HCID 22124471t-Butanol tetrahydrofuran waterHCID 510036741-((1R)-((2R,4R,5S)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methoxy)-4-((1R)-((2R,4S,5R)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methoxy)phthalazineHCID 577138135-(but-3-en-1-ynyl)-4-chloro-7-((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)-7H-pyrrolo [2,3-d]pyrimidin-2-amine

Produkt 1

HCID 57713836(S)-4-(2-amino-4-chloro-7-((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)but-3-yne-1,2-diol

Versuchsvorschrift

Treatment of 5-(but-3-en-1-ynyl)-4-chloro-7-((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)-7H-pyrrolo[2,3-d]pyrimidin-2-amine (see example 46) (35 mg) with AD-mix-α (Aldrich, 540 mg) in t-BuOH:THF:water 1:1:1 (6 mL) at rt overnight, followed by work-up and reverse-phase preparative HPLC gave the title compound (10 mg), as a solid. HPLC Rt=4.13 min

Aufarbeitung

  1. customat rt
  2. customovernight

Quellen und Nachweise

ORD-Eintrag
ord-f4609acb261f472aa88e147f4c520f3b
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07544672B2

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