Isopropyl isocyanate → 3-[4-[4-(Methylsulfonylmethyl)-6-morpholin-4-yl-pyrimidin-2-yl]phenyl]-1-propan-2-yl-urea

HRID 2353637Notes

Reaction equation

HRID 2353637 reaction equation
[CH3:1][S:2]([CH2:5][C:6]1[CH:11]=[C:10]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[N:9]=[C:8]([C:18]2[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][CH:19]=2)[N:7]=1)(=[O:4])=[O:3].[CH:25]([N:28]=[C:29]=[O:30])([CH3:27])[CH3:26]>O1CCOCC1>[CH3:1][S:2]([CH2:5][C:6]1[CH:11]=[C:10]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[N:9]=[C:8]([C:18]2[CH:24]=[CH:23][C:21]([NH:22][C:29](=[O:30])[NH:28][CH:25]([CH3:27])[CH3:26])=[CH:20][CH:19]=2)[N:7]=1)(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 61277Isopropyl isocyanateHCID 593800394-[4-(Methylsulfonylmethyl)-6-morpholin-4-yl-pyrimidine-2-yl]aniline

Product 1

HCID 248046593-[4-[4-(Methylsulfonylmethyl)-6-morpholin-4-yl-pyrimidin-2-yl]phenyl]-1-propan-2-yl-ureaYield 43.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4-[4-(Methylsulfonylmethyl)-6-morpholin-4-yl-pyrimidin-2-yl]aniline (70 mg, 0.2 mmol) and isoproylisocyanate (0.1 mL, 1 mmol) were heated in dioxane (2 mL) at 70° C. for 4 hours. The reaction mixture was evaporated and the residue triturated with ethyl acetate. The suspension was filtered and the white solid washed with ethyl acetate and diethyl ether then dried under vacuum at 60° C. overnight to yield the title compound (38 mg).

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue triturated with ethyl acetate
  3. filtrationThe suspension was filtered
  4. washthe white solid washed with ethyl acetate and diethyl ether
  5. customthen dried under vacuum at 60° C. overnight

Sources & evidence

ORD record
ord-3c09b0b3478244208be315ca3b1b4eb4
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Reaction notes

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