1-Methylpiperazine → HCID 9928658, compound

HRID 567746Notes

Reaction equation

HRID 567746 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[NH:5][C:6]1[C:7]2[CH:14]=[C:13]([CH:15]=O)[NH:12][C:8]=2[N:9]=[CH:10][N:11]=1.[CH3:20][N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1>CO.CN1C(=O)N(C)CCC1.C(O)(=O)C.[Ni]>[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[NH:5][C:6]1[C:7]2[CH:14]=[C:13]([CH2:15][N:24]3[CH2:25][CH2:26][N:21]([CH3:20])[CH2:22][CH2:23]3)[NH:12][C:8]=2[N:9]=[CH:10][N:11]=1

Participants

7

Reactant 2

HCID 531671-MethylpiperazineHCID 110976994-(3-chloroanilino)-6-formyl-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 9928658HCID 9928658, compound

Reagents, catalysts & solvents 4

HCID 935NickelCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Solvent

Procedure

136.4 mg (0.50 mmol) of 4-(3-chloroanilino)-6-formyl-7H-pyrrolo[2,3-d] pyrimidine and 67 μl of N-methylpiperazine in 5 ml of methanol, 15 ml of DMPU and 63 μl of acetic acid are hydrogenated at 50° C. in the presence of 30 mg of Raney nickel. The catalyst is filtered off, the filtrate is evaporated and the residue is dissolved in ethyl acetate and satd NaHCO3 solution. The aqueous phase separated off is extracted twice with ethyl acetate; the organic phases are washed with satd NaHCO3 solution, 4 times with water and brine, dried over Na2SO4 and evaporated. Column chromatography (SiO2, CH2Cl2/methanol=7:2) and stirring in diethyl ether yields 4-(3-chloroanilino)-6-[(4-methylpiperazin-1-yl)methyl]-7H-pyrrolo[2,3-d]pyrimidine; HPLC: tRet(Grad20)=7.4; TLC-Rf=0.16 (CH2Cl2/methanol=7:3); FAB-MS: (M+H)+=357.

Workup

  1. filtrationThe catalyst is filtered off
  2. customthe filtrate is evaporated
  3. dissolutionthe residue is dissolved in ethyl acetate
  4. customThe aqueous phase separated off
  5. extractionis extracted twice with ethyl acetate
  6. washthe organic phases are washed with satd NaHCO3 solution, 4 times with water and brine
  7. dry with materialdried over Na2SO4
  8. customevaporated

Sources & evidence

ORD record
ord-ad0cf83e282e426fa1e6a6eea85b34a6
Source dataset
uspto-grants-2001_01
Patent number
US06180636B2

Reaction notes

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