Cesium carbonate → Tert-butyl (3R)-3-[[5-(7-cyclopropyl-1,3-benzothiazol-2-yl)-6-methoxy-2-(morpholin-4-yl)pyrimidin-4-yl]amino]piperidine-1-carboxylate

HRID 1507536Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1507536
[CH:1]1([C:4]2[C:12]3[S:11][CH:10]=[N:9][C:8]=3[CH:7]=[CH:6][CH:5]=2)[CH2:3][CH2:2]1.I[C:14]1[C:15]([NH:28][C@@H:29]2[CH2:34][CH2:33][CH2:32][N:31]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:30]2)=[N:16][C:17]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)=[N:18][C:19]=1[O:20][CH3:21].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[CH:1]1([C:4]2[C:12]3[S:11][C:10]([C:14]4[C:15]([NH:28][C@@H:29]5[CH2:34][CH2:33][CH2:32][N:31]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:30]5)=[N:16][C:17]([N:22]5[CH2:23][CH2:24][O:25][CH2:26][CH2:27]5)=[N:18][C:19]=4[O:20][CH3:21])=[N:9][C:8]=3[CH:7]=[CH:6][CH:5]=2)[CH2:3][CH2:2]1

Komponenten

7

Edukt 3

HCID 10796Cesium carbonateHCID 89554305(R)-Tert-butyl 3-(5-iodo-6-methoxy-2-morpholinopyrimidin-4-ylamino)piperidine-1-carboxylateHCID 895543067-Cyclopropyl-1,3-benzothiazole

Produkt 1

HCID 117683814Tert-butyl (3R)-3-[[5-(7-cyclopropyl-1,3-benzothiazol-2-yl)-6-methoxy-2-(morpholin-4-yl)pyrimidin-4-yl]amino]piperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418397HCID 178418397, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Following the same procedure as in step 3 of Example 337 using 7-cyclopropyl-1,3-benzothiazole (61.4 mg, 0.35 mmol, 1.80 equiv), tert-butyl (3R)-3-[[5-iodo-6-methoxy-2-(morpholin-4-yl)pyrimidin-4-yl]amino]piperidine-1-carboxylate (100.0 mg, 0.19 mmol, 1.00 equiv) and cesium carbonate (370 mg, 1.14 mmol, 6.00 equiv), Pd(PPh3)4 (40.4 mg, 0.03 mmol, 0.18 equiv) and copper (I) iodide (6.7 mg, 0.04 mmol, 0.18 equiv) in DMF (6 mL). The crude product was purified by flash chromatography on silica gel, eluting with petroleum ether/ethyl acetate (15:1-5:1) to provide the title compound as a light yellow solid. MS m/z [M+H]+ (ESI): 567.

Aufarbeitung

  1. customThe crude product was purified by flash chromatography on silica gel
  2. washeluting with petroleum ether/ethyl acetate (15:1-5:1)

Quellen und Nachweise

ORD-Eintrag
ord-84e0cd1544fb448cabe83e5b9b115f44
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09221809B2

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