Cyclopentylamine → N4-cyclopentylpyrimidine-2,4-diamine

HRID 79191

Reaktionsgleichung

Reaktionsgleichung von HRID 79191
[NH2:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[CH:9]1([NH2:14])[CH2:13][CH2:12][CH2:11][CH2:10]1.C(N(CC)CC)C>CCO>[CH:9]1([NH:14][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH2:1])[N:7]=2)[CH2:13][CH2:12][CH2:11][CH2:10]1

Komponenten

5

Edukt 3

HCID 2906CyclopentylamineHCID 8471TriethylamineHCID 2233322-Amino-4-chloropyrimidine

Produkt 1

HCID 58299890N4-cyclopentylpyrimidine-2,4-diamineAusbeute 84,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
105 °C

Versuchsvorschrift

A mixture of 2-amino-4-chloropyrimidine (22.8 g, 176 mmol), cyclopentylamine (20.9 mL, 211 mmol) and triethylamine (29.4 mL, 211 mmol) in EtOH (200 mL) was heated at reflux (105° C., oil bath) for 48 h. Upon workup, the volatile was removed in vacuo. The residue was poured into ice and saturated Na2CO3 aqueous solution and extracted with ethyl acetate (3×). The combined organics were washed with saturated Na2CO3 aqueous solution (1×), dried over Na2SO4, and concentrated in vacuo to give N4-cyclopentylpyrimidine-2,4-diamine (315) (26.5 g) as a light yellow solid of 92% purity. This batch of material was taken onto the next step without further purification. LCMS-ESI (POS), M/Z, M+1: Found 179.1, Calculated 179.1.

Aufarbeitung

  1. temperaturewas heated
  2. customUpon workup, the volatile was removed in vacuo
  3. additionThe residue was poured into ice and saturated Na2CO3 aqueous solution
  4. extractionextracted with ethyl acetate (3×)
  5. washThe combined organics were washed with saturated Na2CO3 aqueous solution (1×)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-50f69fdebf1f4b2284aa376c6e2cf73c
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841312B2

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