Water → HCID 58588104, compound

HRID 446351Notes

Reaction equation

HRID 446351 reaction equation
[NH2:1][C:2]1[CH:22]=[CH:21][C:5]([O:6][C:7]2[C:12]([C:13]3[CH:18]=[CH:17][N:16]=[C:15]([NH:19][CH3:20])[N:14]=3)=[CH:11][CH:10]=[CH:9][N:8]=2)=[CH:4][CH:3]=1.[N-:23]=[C:24]=[O:25].[K+].O>C(O)(=O)C>[CH3:20][NH:19][C:15]1[N:14]=[C:13]([C:12]2[C:7]([O:6][C:5]3[CH:21]=[CH:22][C:2]([NH:1][C:24]([NH2:23])=[O:25])=[CH:3][CH:4]=3)=[N:8][CH:9]=[CH:10][CH:11]=2)[CH:18]=[CH:17][N:16]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11051572Potassio isocyanateHCID 469295414-(2-(4-aminophenoxy)pyridin-3-yl)-N-methylpyrimidin-2-amine

Product 1

HCID 58588104HCID 58588104, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Dissolved 4-(2-(4-aminophenoxy)pyridin-3-yl)-N-methylpyrimidin-2-amine (75 mg, 0.26 mmol) in acetic acid (1.0 mL), then added potassium isocyanate (0.01 ml, 0.33 mmol), water (0.1 ml), and stirred at RT for 18 hours. Concentrated and purified by reverse phase HPLC (Gilson, acidic mobile phase), extracted into CH2Cl2 washed with NaHCO3 and H2O. Product began to crash out of CH2Cl2 layer, transferred to round bottom flask, concentrated to yield 1-(4-(3-(2-(methylamino)pyrimidin-4-yl)pyridin-2-yloxy)phenyl)urea as off-white solid. MS m/z=337 [M+1]+. Calc'd for C17H36N6O2: 336.35.

Workup

  1. concentrationConcentrated
  2. custompurified by reverse phase HPLC (Gilson, acidic mobile phase)
  3. extractionextracted into CH2Cl2
  4. washwashed with NaHCO3 and H2O
  5. customtransferred to round bottom flask
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8c508be0fa0d4f70a1f8526be15e04b4
Source dataset
uspto-grants-2013_07
Patent number
US08476434B2

Reaction notes

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