Dimethylformamide → HCID 57593794, compound

HRID 1785326Notes

Reaction equation

HRID 1785326 reaction equation
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.[C:5](C1NC=CN=1)(C1NC=CN=1)=[S:6].[NH2:17][C:18]1[CH:23]=[CH:22][C:21]([NH:24][C:25]2[N:30]=[C:29]([NH:31][CH2:32][CH2:33][C:34]3[NH:35][CH:36]=[N:37][CH:38]=3)[C:28]([Br:39])=[CH:27][N:26]=2)=[CH:20][CH:19]=1.CN(C=O)C>C1COCC1>[Br:39][C:28]1[C:29]([NH:31][CH2:32][CH2:33][C:34]2[NH:35][CH:36]=[N:37][CH:38]=2)=[N:30][C:25]([NH:24][C:21]2[CH:20]=[CH:19][C:18]([NH:17][C:5]([NH:4][CH:1]3[CH2:3][CH2:2]3)=[S:6])=[CH:23][CH:22]=2)=[N:26][CH:27]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 69828CyclopropylamineHCID 11412697Thiocarbonyl diimidazoleHCID 57593472N2-(4-Amino-phenyl)-5-bromo-N4-[2-(3H-imidazol-4-yl)ethyl]pyrimidine-2,4-diamine

Product 1

HCID 57593794HCID 57593794, compoundYield 10.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Cyclopropyl amine (0.275 mmole) was dissolved in THF (2 ml) and thiocarbonyl diimidazole (0.28 mmole) was added. The reaction was stirred at room temperature overnight and N2-(4-Amino-phenyl)-5-bromo-N4-[2-(3H-imidazol-4-yl)-ethyl]-pyrimidine-2,4-diamine (0.26 mmole) was added as a solution in THF (3 ml) and DMF (1 ml) and the reaction was stirred overnight. After removal of the solvents under reduced pressure the crude product was purified by flashmaster chromatography (dichloromethane: MeOH 9:1) to yield 12.5 mg of 1-(4-{5-Bromo-4-[2-(3H-imidazol-4-yl)-ethylamino]-pyrimidin-2-ylamino}-phenyl)-3-cyclopropyl-thiourea. ESI-MS: 474.

Workup

  1. customAfter removal of the solvents under reduced pressure the crude product
  2. customwas purified by flashmaster chromatography (dichloromethane: MeOH 9:1)

Sources & evidence

ORD record
ord-1564ff70795a482fa888e2302884bf02
Source dataset
uspto-grants-2009_03
Patent number
US07504410B2

Reaction notes

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