Potassium cyanate → HCID 67389180, compound

HRID 905693Notes

Reaction equation

HRID 905693 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-557df8866006492b87eccbe8f450760e
Source dataset
uspto-grants-2011_09
Patent number
US08012959B2

Reaction notes

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