Phenyl isocyanate → HCID 21946022, compound

HRID 2216982Notes

Reaction equation

HRID 2216982 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([CH:9]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[CH:10]([CH3:12])[CH3:11])=[CH:4][N:3]=1.[C:22]1([N:28]=[C:29]=[O:30])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([CH:9]([N:13]([C:14]2[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=2)[C:29]([NH:28][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:30])[CH:10]([CH3:12])[CH3:11])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 21946005HCID 21946005, compound

Product 1

HCID 21946022HCID 21946022, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
146 °C

Procedure

(±)-[1-(2,4-Dichloro-pyrimidin-5-yl)-2-methyl-propyl]-(4-methoxy-phenyl)-amine (35.0 mg; 0.107 mmol) (from Example 11c supra) and phenyl isocyanate (12.8 μL; 0.12 mmol) (Aldrich) were combined in toluene (0.6 mL), sealed and heated in a microwave reactor (SmithCreator™, 160 seconds to a maximum of 146° C., then 800 seconds at 160° C., and finally 600 seconds at 180° C.). The reaction was incomplete, and the mixture was concentrated and purified by flash chromatography (Biotage 12M; 20:80 ethyl acetate-hexanes) to give the intermediate (±)-1-[1-(2,4-dichloro-pyrimidin-5-yl)-2-methyl-propyl]-1-(4-methoxy-phenyl)-3-phenyl-urea. (Yield 24.0 mg).

Workup

  1. customsealed
  2. custom800 seconds
  3. customat 160° C.
  4. customfinally 600 seconds
  5. customat 180° C.
  6. concentrationthe mixture was concentrated
  7. custompurified by flash chromatography (Biotage 12M; 20:80 ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-8728605f294e417a9f501a372388f23b
Source dataset
uspto-grants-2006_09
Patent number
US07112676B2

Reaction notes

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