Potassium cyanate → HCID 67389180, compound

HRID 269840Notes

Reaction equation

HRID 269840 reaction equation
Cl.Cl.[NH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[N:17]=[C:16]([NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[CH:20]=3)[C:15]([C:26]([NH2:28])=[O:27])=[CH:14][N:13]=2)=[CH:7][CH:6]=1.[O-:29][C:30]#[N:31].[K+]>C(O)(=O)C>[CH3:25][C:21]1[CH:20]=[C:19]([NH:18][C:16]2[C:15]([C:26]([NH2:28])=[O:27])=[CH:14][N:13]=[C:12]([NH:11][C:8]3[CH:9]=[CH:10][C:5]([CH2:4][NH:3][C:30]([NH2:31])=[O:29])=[CH:6][CH:7]=3)[N:17]=2)[CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 11378442Potassium cyanateHCID 67388260HCID 67388260, compound

Product 1

HCID 67389180HCID 67389180, compoundYield 32.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A 20 ml acetic acid-10 ml THF mixed solution containing 500 mg of 2-{[4-(aminomethyl)phenyl]amino}-4-[(3-methylphenyl)-amino]pyrimidine-5-carboxamide dihydrochloride was mixed with 5.76 g of potassium cyanate, which was added by dividing into 6 portions, at room temperature, followed by stirring for 6 hours. The reaction mixture was concentrated and then poured into water, and the precipitated solid was collected by filtration and washed with acetonitrile. The resulting solid was purified by a silica gel column chromatography (chloroform:methanol) to obtain 150 mg of 4-[(3-methylphenyl)amino]-2-[(4-ureidomethylphenyl)amino]pyrimidine-5-carboxamide as a pale yellow solid.

Workup

  1. additionwas added
  2. customby dividing into 6 portions, at room temperature
  3. concentrationThe reaction mixture was concentrated
  4. additionpoured into water
  5. filtrationthe precipitated solid was collected by filtration
  6. washwashed with acetonitrile
  7. customThe resulting solid was purified by a silica gel column chromatography (chloroform:methanol)

Sources & evidence

ORD record
ord-19da83057c2f4f819826f0f46bf038ae
Source dataset
uspto-grants-2008_11
Patent number
US07449456B2

Reaction notes

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