Piperazine → HCID 10403337, compound

HRID 2116457Notes

Reaction equation

HRID 2116457 reaction equation
[NH2:1][C:2]1[C:3]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)=[N:4][C:5]([C:11]#[N:12])=[N:6][C:7]=1[NH:8][CH2:9][CH3:10].[CH:21]([N:24]=C=NC(C)C)(C)C.N1CCNCC1>C(#N)C>[NH2:24][C:21]1[N:8]([CH2:9][CH3:10])[C:7]2[C:2]([N:1]=1)=[C:3]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)[N:4]=[C:5]([C:11]#[N:12])[N:6]=2

Participants

5

Reactant 3

HCID 4837PiperazineHCID 12734DiisopropylcarbodiimideHCID 10334336HCID 10334336, compound

Product 1

HCID 10403337HCID 10403337, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of 5-amino-4-[(4-chlorophenyl)amino]-6-(ethylamino)pyrimidine-2-carbonitrile (0.41 g, prepared using the method of example 20) in acetonitrile (5 ml) was added to a stirred solution of FMOC-NCS (0.44 g) in acetonitrile (10 ml) at 0° C. After 1 h, diisopropylcarbodiimide (0.252 g) was added, the mixture heated under reflux for 4 h, cooled, piperazine (0.1 g) added and stirred at room temperature for 3 h. The solvent was removed under reduced pressure and the residue partitioned between ethyl acetate and brine, the organics dried (MgSO4) and evaporated under reduced pressure. The solid was purified by chromatography on silica eluting with 2-4% methanol in dichloromethane. Yield 0.12 g

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 4 h
  3. temperaturecooled
  4. customThe solvent was removed under reduced pressure
  5. customthe residue partitioned between ethyl acetate and brine
  6. dry with materialthe organics dried (MgSO4)
  7. customevaporated under reduced pressure
  8. customThe solid was purified by chromatography on silica eluting with 2-4% methanol in dichloromethane

Sources & evidence

ORD record
ord-96c20059431d4fa9a0592d8450f46033
Source dataset
uspto-grants-2008_10
Patent number
US07439240B2

Reaction notes

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