Ethylenediamine → 7-(2-aminoethylamino)-5-(6-morpholinopyridin-3-ylamino)pyrido[4,3-d]pyrimidin-4(3H)-one

HRID 1805755Notes

Reaction equation

HRID 1805755 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[N:12]=[CH:11][C:10]([NH:13][C:14]3[C:23]4[C:22](=[O:24])[NH:21][CH:20]=[N:19][C:18]=4[CH:17]=[C:16](Cl)[N:15]=3)=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.[CH2:26]([NH2:29])[CH2:27][NH2:28]>>[NH2:28][CH2:27][CH2:26][NH:29][C:16]1[N:15]=[C:14]([NH:13][C:10]2[CH:11]=[N:12][C:7]([N:4]3[CH2:5][CH2:6][O:1][CH2:2][CH2:3]3)=[CH:8][CH:9]=2)[C:23]2[C:22](=[O:24])[NH:21][CH:20]=[N:19][C:18]=2[CH:17]=1

Participants

3

Reactant 2

HCID 3301EthylenediamineHCID 1361111765-(6-morpholinopyridin-3-ylamino)-7-chloropyrido[4,3-d]pyrimidin-4(3H)-one

Product 1

HCID 1361111747-(2-aminoethylamino)-5-(6-morpholinopyridin-3-ylamino)pyrido[4,3-d]pyrimidin-4(3H)-one

Conditions

Temperature
150 °C

Procedure

A mixture of starting material 5-(6-morpholinopyridin-3-ylamino)-7-chloropyrido[4,3-d]pyrimidin-4(3H)-one (20 mg, 0.055 mmol) and ethylene diamine (200 uL, used as solvent as well) was heated at 150° C. overnight. The excess diamine was removed under reduced pressure, and the residue was subject to HPLC-MS for purification to the final product 7-(2-aminoethylamino)-5-(6-morpholinopyridin-3-ylamino)pyrido[4,3-d]pyrimidin-4(3H)-one.

Workup

  1. customThe excess diamine was removed under reduced pressure
  2. customthe residue was subject to HPLC-MS for purification to the final product 7-(2-aminoethylamino)-5-(6-morpholinopyridin-3-ylamino)pyrido[4,3-d]pyrimidin-4(3H)-one

Sources & evidence

ORD record
ord-443b762ccf0f46a6b72f40bb1d6b78dd
Source dataset
uspto-grants-2013_01
Patent number
US08354526B2

Reaction notes

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