Cyclopropylamine → HCID 18753214, compound

HRID 1838162Notes

Reaction equation

HRID 1838162 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[C:5]([C:9]#[N:10])=[C:4](Cl)[N:3]=1.C([N:14]([CH:18]([CH3:20])[CH3:19])C(C)C)C.[CH:21]1([NH2:24])[CH2:23][CH2:22]1>O1CCOCC1>[Cl:8][C:6]1[C:5]([C:9]#[N:10])=[C:4]([NH:24][CH:21]2[CH2:23][CH2:22]2)[N:3]=[C:2]([NH:14][CH:18]2[CH2:19][CH2:20]2)[N:7]=1

Participants

5

Reactant 3

HCID 69828CyclopropylamineHCID 81531DiisopropylethylamineHCID 2509452,4,6-Trichloro-5-cyanopyrimidine

Product 1

HCID 18753214HCID 18753214, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 500 mg (2.4 mmol) of 2,4,6-trichloro-5-cyano-pyrimidine in 30 ml of dioxane were added at room temperature 0.84 ml (4.8 mmol) of N-ethyl-diisopropylamine and 0.52 ml (7.2 mmol) of cyclopropylamine. The yellow reaction mixture was stirred at room temperature during 18 hours, then, for working-up, it was evaporated under reduced pressure. The residue obtained was then chromatographed on silica gel using a 3:1 mixture of dichloromethane and hexane as the eluent yielding 328 mg (1.3 mmol, 55% of theory) of 4-chloro-2,6-bis-cyclopropylamino-pyrimidine-5-carbonitrile as a yellow solid; MS: [M+H]+=249.

Workup

  1. customit was evaporated under reduced pressure
  2. customThe residue obtained
  3. customwas then chromatographed on silica gel using
  4. additiona 3:1 mixture of dichloromethane and hexane as the eluent

Sources & evidence

ORD record
ord-845e7d70164c4169aec30915f5ab8462
Source dataset
uspto-grants-2004_01
Patent number
US06673795B2

Reaction notes

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