Water → 2-(2,6-Dichlorobenzyl)-N-[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl][1,3]thiazolo[5,4-d]pyrimidin-7-amine

HRID 474312

Reaktionsgleichung

Reaktionsgleichung von HRID 474312
Cl[C:2]1[C:3]2[N:10]=[C:9]([CH2:11][C:12]3[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=3[Cl:19])[S:8][C:4]=2[N:5]=[CH:6][N:7]=1.[F:20][C:21]([F:29])([F:28])[C:22]1[S:26][C:25]([NH2:27])=[N:24][N:23]=1.[H-].[Na+].O>CN(C=O)C>[Cl:19][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]([Cl:18])[C:12]=1[CH2:11][C:9]1[S:8][C:4]2[N:5]=[CH:6][N:7]=[C:2]([NH:27][C:25]3[S:26][C:22]([C:21]([F:29])([F:28])[F:20])=[N:23][N:24]=3)[C:3]=2[N:10]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 826341,3,4-Thiadiazol-2-amine, 5-(trifluoromethyl)-HCID 577424637-Chloro-2-(2,6-dichloro-benzyl)-thiazolo[5,4-d]pyrimidine

Produkt 1

HCID 426419252-(2,6-Dichlorobenzyl)-N-[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl][1,3]thiazolo[5,4-d]pyrimidin-7-amineAusbeute 41 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 7-chloro-2-(2,6-dichloro-benzyl)-thiazolo[5,4-d]pyrimidine (83 mg, 0.3 mmol) and 5-trifluoromethyl-[1,3,4]thiadiazol-2-ylamine (63 mg, 0.4 mmol) in DMF (1 mL) was added NaH (60% dispersion in oil; 20 mg, 0.5 mmol) at rt. After 12 h, the reaction mixture was poured into H2O (5 mL) and the resulting solid was collected by vacuum filtration and washed with 1:1 (IPA-H2O) to afford the title compound as a yellow solid (48 mg, 41%). MS (ESI): mass calcd. for C15H7Cl2F3N6S2, 462.0; m/z found, 462.9 [M+H]+. 1H NMR ((CD3)2SO): 8.45 (s, 1H), 7.58 (d, J=8.0 Hz, 2H), 7.46-7.41 (m, 1H), 4.72 (s, 2H).

Aufarbeitung

  1. filtrationthe resulting solid was collected by vacuum filtration
  2. washwashed with 1:1 (IPA-H2O)

Quellen und Nachweise

ORD-Eintrag
ord-036c002d0be34b7394183e87627e2cdc
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637527B2

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