Acetic Acid → 4-(3-Chloro-phenylamino)-3-(2-ureido-ethylamino)-1H-pyrazolo[3,4-d]-pyrimidine

HRID 1068962Notes

Reaction equation

HRID 1068962 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5]1[C:13]2[C:8](=[N:9][CH:10]=[N:11][C:12]=2[NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=2)[NH:7][N:6]=1.[O-:22][C:23]#[N:24].[K+].C(O)C.C(O)(=O)C>O>[Cl:21][C:17]1[CH:16]=[C:15]([NH:14][C:12]2[N:11]=[CH:10][N:9]=[C:8]3[NH:7][N:6]=[C:5]([NH:4][CH2:3][CH2:2][NH:1][C:23]([NH2:24])=[O:22])[C:13]=23)[CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 702EthanolHCID 11378442Potassium cyanateHCID 211906263-(2-amino-ethylamino)-4-(3-chloro-phenylamino)-1H-pyrazolo[3,4-d]pyrimidine

Product 1

HCID 211906104-(3-Chloro-phenylamino)-3-(2-ureido-ethylamino)-1H-pyrazolo[3,4-d]-pyrimidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 200 mg (0.655 mmol) of 3-(2-amino-ethylamino)-4-(3-chloro-phenylamino)-1H-pyrazolo[3,4-d]pyrimidine (water content: 0.48%), 72 mg (0.887 mmol) of potassium cyanate, 1.2 ml of ethanol, 1.2 ml of water and 46.8 ml (0.819 mmol) of acetic acid is stirred at RT for 15 hours. 2 ml of water are added to the resulting suspension and the mixture is filtered. Washing the filter residue with water and a small amount of ethanol and drying in vacuo (about 100 mbar, 8 hours, 1 00C) yield the title compound having a water content of 5.54%; m.p. 212-214° C.; ESI-MS: (M+H)+=347

Workup

  1. filtrationthe mixture is filtered
  2. washWashing the filter residue with water
  3. dry with materiala small amount of ethanol and drying in vacuo (about 100 mbar, 8 hours, 1 00C)

Sources & evidence

ORD record
ord-8599497299784618a699d931c7b83113
Source dataset
uspto-grants-2001_06
Patent number
US06251911B1

Reaction notes

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