Allyl Isothiocyanate → 1-Allyl-3-[4-(5-bromo-4-prop-2-ynylamino-pyrimidin-2-ylamino)-phenyl]-thiourea

HRID 1785333Notes

Reaction equation

HRID 1785333 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:14]=[C:13]([NH:15][CH2:16][C:17]#[CH:18])[C:12]([Br:19])=[CH:11][N:10]=2)=[CH:4][CH:3]=1.[CH2:20]([N:23]=[C:24]=[S:25])[CH:21]=[CH2:22]>C(#N)C>[CH2:20]([NH:23][C:24]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:14]=[C:13]([NH:15][CH2:16][C:17]#[CH:18])[C:12]([Br:19])=[CH:11][N:10]=2)=[CH:4][CH:3]=1)=[S:25])[CH:21]=[CH2:22]

Participants

4

Reactant 2

HCID 5971Allyl IsothiocyanateHCID 57593369N2-(4-Amino-phenyl)-5-bromo-N4-prop-2-ynyl-pyrimidine-2,4-diamine

Product 1

HCID 575935531-Allyl-3-[4-(5-bromo-4-prop-2-ynylamino-pyrimidin-2-ylamino)-phenyl]-thiourea

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N2-(4-Amino-phenyl)-5-bromo-N4-prop-2-ynyl-pyrimidine-2,4-diamine (100 mg, 0.3 mmole, prepared in analogy procedure 21) was dissolved in acetonitrile (10 ml) and allyl isothiocyanate (1 ml) was added at room temperature. The reaction mixture was heated under reflux for 3 hours, the solvent removed under reduced pressure and 1-Allyl-3[4-(5-bromo-4-prop-2-ynylamino-pyrimidin-2-ylamino)-phenyl]-thiourea was crystallized from acetone/ethyl acetate/hexanes. Yield 37 mg. ESI-MS: 418.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 3 hours
  3. customthe solvent removed under reduced pressure and 1-Allyl-3[4-(5-bromo-4-prop-2-ynylamino-pyrimidin-2-ylamino)-phenyl]-thiourea
  4. customwas crystallized from acetone/ethyl acetate/hexanes

Sources & evidence

ORD record
ord-69dd0512a0984eb9a6ff0183a16df756
Source dataset
uspto-grants-2009_03
Patent number
US07504410B2

Reaction notes

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