tert-butyl N-(5-(tributylstannyl)-1,3-thiazol-2-yl)carbamate → 5-(4-morpholino-6-((4-N-methylsulfonylpiperazin-1-yl)methyl)thieno[3,2-d]pyrimidin-2-yl)thiazol-2-amine

HRID 390865

Reaktionsgleichung

Cl[C:2]1[N:3]=[C:4]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[C:5]2[S:10][C:9]([CH2:11][N:12]3[CH2:17][CH2:16][N:15]([S:18]([CH3:21])(=[O:20])=[O:19])[CH2:14][CH2:13]3)=[CH:8][C:6]=2[N:7]=1.C(OC(=O)[NH:34][C:35]1[S:36][C:37]([Sn](CCCC)(CCCC)CCCC)=[CH:38][N:39]=1)(C)(C)C>CC(N(C)C)=O.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>[O:25]1[CH2:26][CH2:27][N:22]([C:4]2[C:5]3[S:10][C:9]([CH2:11][N:12]4[CH2:17][CH2:16][N:15]([S:18]([CH3:21])(=[O:20])=[O:19])[CH2:14][CH2:13]4)=[CH:8][C:6]=3[N:7]=[C:2]([C:37]3[S:36][C:35]([NH2:34])=[N:39][CH:38]=3)[N:3]=2)[CH2:23][CH2:24]1

Komponenten

Reaktionsbedingungen

Temperatur: 150 °C

Versuchsvorschrift

A suspension of 2-chloro-6-(4-methanesulfonyl-piperazin-1-ylmethyl)-4-morpholin-4-yl-thieno[3,2-d]pyrimidine, prepared via General Procedure B-3, (201 mg, 0.465 mmol), (5-tributylstannyl-thiazol-2-yl)-carbamic acid tert-butyl ester (341 mg, 0.7 mmol), and Pd(PPh3)4 (27 mg, 0.023 mmol) in anhydrous DMA was heated in a microwave at 150° C. for 10 mins. Ethyl acetate/water extraction and purification on silica using 10% methanol in ethyl acetate as the eluent to give 153 as an off-white solid (84 mg, 36%). NMR (MeOD), 2.68-2.72 (4H, m), 2.88 (3H, s), 3.26-3.31 (4H, m), 3.83-3.87 (4H, m), 3.95 (2H, s), 3.99-4.03 (4H, m), 4.65 (2H, br s), 7.25 (1H, s), 7.82 (1H, s). MS: (ESI+): MH+ 496

Aufarbeitung

extractionEthyl acetate/water extraction and purification on silica using 10% methanol in ethyl acetate as the eluent

Quellen und Nachweise

ORD-Eintrag: ord-35d3cafec9204c18b133861c0fa98ae4
Quelldatensatz: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08383620B2

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