Sodium Hydroxide → 4-(3-Methylanilino)-2-[(2-ureidoethyl)amino]pyrimidine-5-carboxamide

HRID 2303312Notes

Reaction equation

HRID 2303312 reaction equation
[O-:1][C:2]#[N:3].[K+].Cl.O1CCOCC1.[NH2:12][CH2:13][CH2:14][NH:15][C:16]1[N:21]=[C:20]([NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[CH:24]=2)[C:19]([C:30]([NH2:32])=[O:31])=[CH:18][N:17]=1.[OH-].[Na+]>O1CCOCC1.O>[CH3:29][C:25]1[CH:24]=[C:23]([CH:28]=[CH:27][CH:26]=1)[NH:22][C:20]1[C:19]([C:30]([NH2:32])=[O:31])=[CH:18][N:17]=[C:16]([NH:15][CH2:14][CH2:13][NH:12][C:2]([NH2:3])=[O:1])[N:21]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 98173492-(2-Aminoethylamino)-4-(m-tolylamino)pyrimidine-5-carboxamideHCID 11378442Potassium cyanateHCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 184608294-(3-Methylanilino)-2-[(2-ureidoethyl)amino]pyrimidine-5-carboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A 147 mg portion of potassium cyanate and 450 μl of 4 M hydrochloric acid-dioxane solution were added to a mixture of 312 mg of 2-(2-aminoethylamino)-4-(3-methylanilino)pyrimidine-5-carboxamide and 3 ml of water and 3 ml of 1,4-dioxane, followed by stirring at room temperature for 1 day. The reaction mixture was alkalified by adding 1 M sodium hydroxide aqueous solution, and the thus formed precipitate was collected by filtration. The filtered material was washed by stirring it in methanol while heating and then collected by filtration to obtain 212 mg of 4-(3-methylanilino)-2-[(2-ureidoethyl)amino]pyrimidine-5-carboxamide (colorless solid).

Workup

  1. filtrationthe thus formed precipitate was collected by filtration
  2. washThe filtered material was washed
  3. stirringby stirring it in methanol
  4. temperaturewhile heating
  5. filtrationcollected by filtration

Sources & evidence

ORD record
ord-ba3eff2c6e214304bc183c3df6a17171
Source dataset
uspto-grants-2002_08
Patent number
US06432963B1

Reaction notes

Loading…