Azidotrimethylsilane → Hydrochloric Acid

HRID 1509062Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1509062
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([CH2:25][C:26]#[N:27])=[CH:21][CH:20]=3)[C:11]3[S:17][CH2:16][CH2:15][CH2:14][C:12]=3[N:13]=2)[CH:5]=[CH:6][CH:7]=1.[N:28]([Si](C)(C)C)=[N+:29]=[N-:30].O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([CH2:25][C:26]4[N:28]=[N:29][NH:30][N:27]=4)=[CH:21][CH:20]=3)[C:11]3[S:17][CH2:16][CH2:15][CH2:14][C:12]=3[N:13]=2)[CH:5]=[CH:6][CH:7]=1.[ClH:1]

Komponenten

5

Edukt 3

HCID 78378AzidotrimethylsilaneHCID 162116731-Butanaminium, N,N,N-tributyl-, fluoride, hydrateHCID 901102942-[4-[[2-(3-Chlorophenyl)-7,8-dihydro-6H-thiopyrano[3,2-d]pyrimidin-4-yl]amino]phenyl]acetonitrile

Produkt 2

HCID 313Hydrochloric AcidAusbeute 65 %HCID 742215632-(3-chlorophenyl)-N-[4-(2H-tetrazol-5-ylmethyl)phenyl]-7,8-dihydro-6H-thiopyrano[3,2-d]pyrimidin-4-amine

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

A 8-mL vial was charged with 2-[4-[[2-(3-chlorophenyl)-7,8-dihydro-6H-thiopyrano[3,2-d]pyrimidin-4-yl]amino]phenyl]acetonitrile (32 mg, 0.081 mmol, 1 eq.), azido(trimethyl)silane (0.2 ml, excess) and tetrabutylammonium fluoride hydrate (50 mg, 0.19 mmol, 2.3 eq.). The mixture was stirred at 110° C. overnight. After cooling to room temperature, the mixture was partitioned between dichloromethane (4 ml) and 2N HCl (4 ml). The solid was collected by filtration and washed with water (10 ml) followed dichloromethane (10 ml). After drying, the title compound was obtained as HCl salt (25 mg, 65% yield).). MW/HCl=472.39. 1H NMR (400 MHz, DMSO-D6) δ 8.6 (brs, 1H), 8.16 (s, 1H), 8.11 (d, J=7.2 Hz, 1H), 7.64 (d, J=8.4 Hz, 2H), 7.53 (m, 2H), 7.29 (d, J=8.4 Hz, 2H), 4.31 (s, 2H), 3.21 (d, J=5.6 Hz, 2H), 2.94 (d, J=6.4 Hz, 2H), 2.19 (m, 2H).

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. customthe mixture was partitioned between dichloromethane (4 ml) and 2N HCl (4 ml)
  3. filtrationThe solid was collected by filtration
  4. washwashed with water (10 ml)
  5. customAfter drying

Quellen und Nachweise

ORD-Eintrag
ord-50f2a371968f4f9aa9c1a022ee240771
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09221843B2

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