Hydrochloric Acid → 5-Bromo-n4-cyclopropyl-n2-(3-methylsulphanylphenyl)pyrimidine-2,4-diamine

HRID 548951Notes

Reaction equation

HRID 548951 reaction equation
[Br:1][C:2]1[C:3]([NH:9][CH:10]2[CH2:12][CH2:11]2)=[N:4][C:5](Cl)=[N:6][CH:7]=1.[CH3:13][S:14][C:15]1[CH:16]=[C:17]([NH2:21])[CH:18]=[CH:19][CH:20]=1.Cl.O>C(#N)C.O1CCOCC1>[Br:1][C:2]1[C:3]([NH:9][CH:10]2[CH2:12][CH2:11]2)=[N:4][C:5]([NH:21][C:17]2[CH:18]=[CH:19][CH:20]=[C:15]([S:14][CH3:13])[CH:16]=2)=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 15693Benzenamine, 3-(methylthio)-HCID 584599345-bromo-2-chloro-N-cyclopropylpyrimidin-4-amine

Product 1

HCID 596831485-Bromo-n4-cyclopropyl-n2-(3-methylsulphanylphenyl)pyrimidine-2,4-diamine

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 312751,4-DioxaneSolvent

Procedure

In analogy to compound 2.1, 0.58 g (2.33 mmol) of (5-bromo-2-chloropyrimidin-4-yl)-cyclopropylamine is reacted with 0.296 g (2.12 mmol) of 3-methylsulphanyl-phenylamine in 7.0 ml of acetonitrile in the presence of 0.53 mol of a 4 molar solution of hydrogen chloride in dioxane, and 0.67 ml of water. 0.6 g (73% of theory) of the product is obtained.

Workup

  1. custom0.6 g (73% of theory) of the product is obtained

Sources & evidence

ORD record
ord-bf3dfe5ac7c3406e999f7f90533ee1b7
Source dataset
uspto-grants-2011_05
Patent number
US07943629B2

Reaction notes

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