Dimethylformamide → HCID 57593794, compound

HRID 1785328Notes

Reaction equation

HRID 1785328 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-81227650337c4c01a0bd12b44a807581
Source dataset
uspto-grants-2009_03
Patent number
US07504410B2

Reaction notes

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