Methane → 6-(4-Amino-4-methylpiperidin-1-yl)-4-(3-chloro-4-fluorophenylamino)-pyrimido[5,4-d]pyrimidine

HRID 1840637

Reaktionsgleichung

Reaktionsgleichung von HRID 1840637
[NH2:1][C:2]1([CH3:28])[CH2:7][CH2:6][N:5]([C:8]2[NH:9][CH2:10][C:11]3[N:12]=[C:13](Cl)[N:14]=[C:15]([NH:18][C:19]4[CH:24]=[CH:23][C:22]([F:25])=[C:21]([Cl:26])[CH:20]=4)[C:16]=3[N:17]=2)[CH2:4][CH2:3]1.I.C>C(O)(=O)C>[NH2:1][C:2]1([CH3:28])[CH2:3][CH2:4][N:5]([C:8]2[N:9]=[CH:10][C:11]3[N:12]=[CH:13][N:14]=[C:15]([NH:18][C:19]4[CH:24]=[CH:23][C:22]([F:25])=[C:21]([Cl:26])[CH:20]=4)[C:16]=3[N:17]=2)[CH2:6][CH2:7]1

Komponenten

5

Edukt 3

HCID 297MethaneHCID 24841Hydrogen iodideHCID 178432946HCID 178432946, Verbindung

Produkt 1

HCID 99522166-(4-Amino-4-methylpiperidin-1-yl)-4-(3-chloro-4-fluorophenylamino)-pyrimido[5,4-d]pyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
15 °C

Versuchsvorschrift

A mixture of 80 g (0.182 mol) of (6) in 160 ml glacial acetic acid at 90° C. is added dropwise to a suspension of 11.7 g (0.378 mol) of red phosphorus in 150 ml of hydriodic acid (57%, 1.134 mol). The mixture is refluxed for 4 hours, 5 g of activated charcoal are added, the mixture is then filtered and the residue is washed with glacial acetic acid and water. The filtrate is added dropwise, with vigorous stirring, to a solution of 270 ml water, 270 ml of methanol and 270 ml of sodium hydroxide solution (50%). The mixture is stirred for a further 30 minutes at 15° C. and the solid precipitated is filtered off. This is washed twice with 500 ml of water, then suspended in 500 ml of water, filtered off and dried in vacuo at 45° C. Yield: 65.2 g (91.9%)

Aufarbeitung

  1. temperatureThe mixture is refluxed for 4 hours
  2. filtrationthe mixture is then filtered
  3. washthe residue is washed with glacial acetic acid and water
  4. additionThe filtrate is added dropwise, with vigorous stirring, to a solution of 270 ml water, 270 ml of methanol and 270 ml of sodium hydroxide solution (50%)
  5. customthe solid precipitated
  6. filtrationis filtered off
  7. washThis is washed twice with 500 ml of water
  8. filtrationfiltered off
  9. customdried in vacuo at 45° C

Quellen und Nachweise

ORD-Eintrag
ord-8f9d583311f04e19926570d9e298837c
Quelldatensatz
uspto-grants-2004_01
Patentnummer
US06680384B2

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