Phenyl isocyanate → HCID 15239976, compound

HRID 1653636Notes

Reaction equation

HRID 1653636 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[C:5]([O:12][C:13]2[N:18]=[C:17]([O:19][CH3:20])[CH:16]=[C:15]([O:21][CH3:22])[N:14]=2)=[CH:4][CH:3]=1.[C:23]1([N:29]=[C:30]=[O:31])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.N12CCN(CC1)CC2>CCC(C)=O>[CH3:22][O:21][C:15]1[CH:16]=[C:17]([O:19][CH3:20])[N:18]=[C:13]([O:12][C:5]2[C:6]([C:8]([O:10][CH3:11])=[O:9])=[N:7][C:2]([NH:1][C:30](=[O:31])[NH:29][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:3][CH:4]=2)[N:14]=1

Participants

5

Reactant 3

HCID 7672Phenyl isocyanateHCID 9237DabcoHCID 15239974Methyl 3-[(4,6-dimethoxypyrimidin-2-yl)oxy]-6-aminopicolinate

Product 1

HCID 15239976HCID 15239976, compoundYield 71.1%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

2 g (6.5 mmol) of methyl 6-amino-3-[(4,6-dimethoxypyrimidin-2-yl)oxy]picolinate, 0.77 g (7.15 mmol) of phenyl isocyanate and a catalytic amount of crystals of 1,4-diazabicyclo-[2.2.2]-octane were added to 50 ml of MEK, and the mixture was stirred and refluxed for 4 hours. After completion of the reaction, the product was filtered and washed with MEK to obtain the desired product as colorless transparent crystals.

Workup

  1. temperaturerefluxed for 4 hours
  2. customAfter completion of the reaction
  3. filtrationthe product was filtered
  4. washwashed with MEK

Sources & evidence

ORD record
ord-27f49a1f1cfd4bf48d55e59252843a0a
Source dataset
uspto-grants-1995_04
Patent number
US05403816

Reaction notes

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