Water → HCID 58588104, compound

HRID 1361708Notes

Reaction equation

HRID 1361708 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, transfered 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 C17H16N6O2: 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. customto crash out of CH2Cl2 layer, transfered to round bottom flask
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f6628d04851d4e6d932f7864b77bb0e8
Source dataset
uspto-grants-2011_02
Patent number
US07880000B2

Reaction notes

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