Phenyl isocyanate → HCID 58504371, compound

HRID 2367394Notes

Reaction equation

HRID 2367394 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[C@H:13]([CH3:14])[CH2:12][O:11][C@H:10]([CH2:15][OH:16])[CH2:9]2)[CH:5]=[C:4]([Cl:17])[N:3]=1.CCN(C(C)C)C(C)C.[C:27]1([N:33]=[C:34]=[O:35])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C(Cl)(Cl)Cl>[C:27]1([NH:33][C:34](=[O:35])[O:16][CH2:15][C@H:10]2[O:11][CH2:12][C@@H:13]([CH3:14])[N:8]([C:6]3[CH:5]=[C:4]([Cl:17])[N:3]=[C:2]([NH2:1])[N:7]=3)[CH2:9]2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 7672Phenyl isocyanate2×HCID 81531Diisopropylethylamine2×HCID 51353725HCID 51353725, compound

Product 1

HCID 58504371HCID 58504371, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
0 °C

Procedure

To a 20-mL screw-cap vial was added [(2S,5R)-4-(2-amino-6-chloro-4-pyrimidinyl)-5-methyl-2-morpholinyl]methanol (100 mg, 0.387 mmol), Hunig's base (0.135 mL, 0.773 mmol) and CHCl3 (10 mL). The reaction was cooled to 0° C., then phenyl isocyanate (0.046 mL, 0.425 mmol) in CHCl3 (2 mL) was added dropwise via syringe. The solution was allowed to warm to room temperature and then stirred overnight. An additional portion of Hunig's base (0.135 mL, 0.773 mmol) and phenyl isocyanate (0.046 mL, 0.425 mmol) was added, and the reaction stirred at 60° C. overnight. The solvents were removed in vacuo, and the residue was purified by flash chromatography to afford the title compound (123 mg). LC-MS (ES) m/z=378 [M+H]+.

Workup

  1. customTo a 20-mL screw-cap vial
  2. temperatureto warm to room temperature
  3. stirringthe reaction stirred at 60° C. overnight
  4. customThe solvents were removed in vacuo
  5. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-c5de1ada44d84d989e3e6e9d7c8711ad
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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