6-Methyl-5-nitro-N*2*-(4-trifluoromethylbenzyl)-pyrimidine-2,4-diamine → 6-Methyl-N*2*-(4-trifluoromethylbenzyl)-pyrimidine-2,4,5-triamine

HRID 2245221Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2245221
[CH3:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)[N:5]=[C:4]([NH2:20])[C:3]=1[N+:21]([O-])=O>O1CCCC1.C(O)(=O)C.[Zn]>[CH3:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][C:10]2[CH:11]=[CH:12][C:13]([C:16]([F:18])([F:19])[F:17])=[CH:14][CH:15]=2)[N:5]=[C:4]([NH2:20])[C:3]=1[NH2:21]

Komponenten

5

Edukt 1

HCID 592160226-Methyl-5-nitro-N*2*-(4-trifluoromethylbenzyl)-pyrimidine-2,4-diamine

Produkt 1

HCID 592160216-Methyl-N*2*-(4-trifluoromethylbenzyl)-pyrimidine-2,4,5-triamineAusbeute 105,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23994ZincKatalysatorHCID 176Acetic AcidLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a vigorously stirred solution of 6-methyl-5-nitro-N*2*-(4-trifluoromethylbenzyl)-pyrimidine-2,4-diamine (450 mg, 1.376 mmol) in tetrahydrofuran (20 ml) and acetic acid (5 ml) on cold water bath, zinc powder (particle size<10 micron, 5 g) was added by portions in 2 min. Water bath was removed and more zinc powder (2 g) were added. The suspension was stirred at ambient temperature for 60 min and quenched with 10% aqueous sodium carbonate to pH>8. The obtained suspension was extracted with ethyl acetate (10 times). The combined organic solution was filtered via plug of silica gel (10 g) and eluted with 20% in ethyl acetate to give 430 mg of pale yellow oil after evaporation. The product solidified after drying in vacuo. Yield 100%. It was used in the next step without further purification. LC-MS (m/z) 298.1 (MH+); tR=1.68. 1H NMR (500 MHz, DMSO-d6): 2.02 (s, 3H), 3.1-3.8 (br, NH2+H2O), 4.43 (d, 2H), 5.88 (br, 2H), 6.26 (t, 1H, NH), 7.48 (d, 2H), 7.62 (d, 2H).

Aufarbeitung

  1. customWater bath was removed
  2. additionmore zinc powder (2 g) were added
  3. customquenched with 10% aqueous sodium carbonate to pH>8
  4. extractionThe obtained suspension was extracted with ethyl acetate (10 times)
  5. filtrationThe combined organic solution was filtered via plug of silica gel (10 g)
  6. washeluted with 20% in ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-8dd0b06adbab40a597731759699ba4d0
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07683058B2

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