Diglycolamine → 2-Amino-4-[2-(2-hydroxyethoxy)ethylamino]-5-phenylethynyl pyrimidine

HRID 1271036

Reaktionsgleichung

Reaktionsgleichung von HRID 1271036
Cl[C:2]1[C:7]([C:8]#[C:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][N:5]=[C:4]([N:16]=CN(C(C)C)C(C)C)[N:3]=1.[NH2:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][OH:31]>C(O)C>[NH2:16][C:4]1[N:3]=[C:2]([NH:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][OH:31])[C:7]([C:8]#[C:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[CH:6][N:5]=1

Komponenten

4

Edukt 2

HCID 13578DiglycolamineHCID 734464524-Chloro-2-diisopropylaminomethyleneamino-5-phenylethynylpyrimidine

Produkt 1

HCID 98574242-Amino-4-[2-(2-hydroxyethoxy)ethylamino]-5-phenylethynyl pyrimidineAusbeute 37,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 1.5 g of 4-chloro-2-diisopropylaminomethyleneamino-5-phenylethynylpyrimidine, 20 mL of ethanol and 1.83 g of 2-(2-aminoethoxy)ethanol was refluxed for 18 hours. The tea colored solution was evaporated in vacuo and the residue partitioned between water and dichloromethane. The aqueous layer was washed twice more with dichloromethane and the combined organic extracts washed with water. The organic solution was dried over sodium sulfate, filtered and evaporated in vacuo. The yellow residue obtained was triturated with ether and filtered to give 0.49 g of a yellow solid, 2-amino-4-[2-(2-hydroxyethoxy)ethylamino]-5-phenylethynylpyrimidine. m.p. 128–129° C.

Aufarbeitung

  1. temperaturewas refluxed for 18 hours
  2. customThe tea colored solution was evaporated in vacuo
  3. customthe residue partitioned between water and dichloromethane
  4. washThe aqueous layer was washed twice more with dichloromethane
  5. washthe combined organic extracts washed with water
  6. dry with materialThe organic solution was dried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customThe yellow residue obtained
  10. customwas triturated with ether
  11. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-fb1d7b06e0004458b46d0c6a48157306
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07205297B2

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