Water → HCID 57593328, compound

HRID 1785332Notes

Reaction equation

HRID 1785332 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.C(N(CC)CC)C.Cl[C:28]([O:30][CH2:31][CH2:32][CH2:33][CH3:34])=[O:29].O>C1COCC1>[CH2:31]([O:30][C:28](=[O:29])[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)[CH2:32][CH2:33][CH3:34]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 61140Butyl chloroformateHCID 57593369N2-(4-Amino-phenyl)-5-bromo-N4-prop-2-ynyl-pyrimidine-2,4-diamine

Product 1

HCID 57593328HCID 57593328, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N2-(4-Amino-phenyl)-5-bromo-N4-prop-2-ynyl-pyrimidine-2,4-diamine (0.31 mmol, prepared in analogy to procedure 21) was dissolved in THF (20 ml), triethyl amine (0.33 mmole) and butyl chloroformate (0.33 mmole) were added at room temperature and the reaction was stirred at this temperature until the starting material disappeared (TLC, 3 h). The reaction was poured into water and [4-(5-Bromo-4-prop-2-ynylamino-pyrimidin-2-ylamino)-phenyl]-carbamic acid butyl ester was isolated by filtration. Yield: 91 mg (70%). ESI-MS: 419.

Workup

  1. custom(TLC, 3 h)

Sources & evidence

ORD record
ord-ed114cfebe3847bd91204ad2ff5a44c3
Source dataset
uspto-grants-2009_03
Patent number
US07504410B2

Reaction notes

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