Ethyl isocyanate → HCID 59379944, compound

HRID 2353633Notes

Reaction equation

HRID 2353633 reaction equation
[CH3:1][Si:2]([CH3:29])([C:25]([CH3:28])([CH3:27])[CH3:26])[O:3][CH2:4][C:5]1[CH:10]=[C:9]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][C@@H:12]2[CH3:17])[N:8]=[C:7]([C:18]2[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][CH:19]=2)[N:6]=1.[CH2:30]([N:32]=[C:33]=[O:34])[CH3:31]>O1CCOCC1>[CH3:29][Si:2]([CH3:1])([C:25]([CH3:28])([CH3:27])[CH3:26])[O:3][CH2:4][C:5]1[CH:10]=[C:9]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][C@@H:12]2[CH3:17])[N:8]=[C:7]([C:18]2[CH:19]=[CH:20][C:21]([NH:22][C:33]([NH:32][CH2:30][CH3:31])=[O:34])=[CH:23][CH:24]=2)[N:6]=1

Participants

4

Reactant 2

HCID 8022Ethyl isocyanateHCID 59379958HCID 59379958, compound

Product 1

HCID 59379944HCID 59379944, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

4-[4-[(Dimethyl-tert-butyl-silyl)oxymethyl]-6-[(3S)-3-methylmorpholin-4-yl]pyrimidin-2-yl]aniline (250 mg) was dissolved in 1,4-dioxane (4 mL) and ethyl isocyanate (0.144 mL) added. The reaction was heated to 120° C. for 1 hour in a microwave reactor. The reaction was concentrated in vacuo then the residue chromatographed on silica, eluting with 2.5% methanol in DCM, to give the desired compound (106 mg) as a white solid.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customthe residue chromatographed on silica
  3. washeluting with 2.5% methanol in DCM

Sources & evidence

ORD record
ord-e46e165b825d41e1bb5c3ac9ff63ea56
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Reaction notes

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