Ammonia → 6-Chloro-2-phenylpyrimidin-4-amine

HRID 895460

Reaktionsgleichung

Reaktionsgleichung von HRID 895460
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[N:5]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:3]=1.[NH3:15].O>CS(C)=O>[Cl:1][C:2]1[N:3]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:5]=[C:6]([NH2:15])[CH:7]=1

Komponenten

5

Edukt 3

HCID 222AmmoniaHCID 962WaterHCID 77338Fenclorim

Produkt 1

HCID 3177476-Chloro-2-phenylpyrimidin-4-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

An ice-cold suspension of pyrimidine 3 (44.34 g; 0.197 mol) in DMSO (366 mL) was saturated with ammonia, during which time a solution formed. After 24 h at rt, water (710 mL) was added dropwise. The suspension was cooled in an ice bath for 1 h then collected by filtration and washed with water (500 mL), yielding a light tan powder after drying in vacuo (37.84 g; 93%). LC (method B) tR=16.0 min; 1H NMR (200 MHz, CDCl3) δ 8.33 (m, 2H), 8.44 (m, 3H), 6.32 (s, 1H), 5.12 (brs, 2H); 13C NMR (50.3 MHz, CDCl3) δ 165.1, 164.0, 160.5, 136.7, 131.0, 128.4, 128.4, 101.4; ESIMS 205.9/207.8 (100/34) [MH+].

Aufarbeitung

  1. customformed
  2. temperatureThe suspension was cooled in an ice bath for 1 h
  3. filtrationthen collected by filtration
  4. washwashed with water (500 mL)
  5. customyielding a light tan powder
  6. customafter drying in vacuo (37.84 g; 93%)

Quellen und Nachweise

ORD-Eintrag
ord-ead9dbd8072d4e5994d5a819cfe0a097
Quelldatensatz
uspto-grants-2005_07
Patentnummer
US06916804B2

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