Acetic Acid → HCID 21262613, compound

HRID 567754Notes

Reaction equation

HRID 567754 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][O:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26][NH2:27])=[CH:24][CH:23]=1.C(O)(=O)C>CO.CN1C(=O)N(C)CCC1.[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][NH:27][CH2:26][C:25]3[CH:28]=[CH:29][C:22]([O:21][CH3:20])=[CH:23][CH:24]=3)[NH:12][C:8]=2[N:9]=[CH:10][N:11]=1

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 754524-MethoxybenzylamineHCID 110976994-(3-chloroanilino)-6-formyl-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 21262613HCID 21262613, compound

Reagents, catalysts & solvents 3

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

Procedure

273 mg (1.00 mmol) of 4-(3-chloroanilino)-6-formyl-7H-pyrrolo[2,3-d]pyrimidine (stage 1.6) and 156 ml (1.2 mmol) of 4-methoxybenzylamine in 10 ml of methanol, DMPU and 126 μl (2.2 mmol) of acetic acid are stirred at RT for 1 h. 0.1 g of Raney nickel is then added and the mixture is hydrogenated at RT and finally at 50° C. The catalyst is filtered off, the filtrate is evaporated and the residue is dissolved in ethyl acetate and satd Na2CO3 solution. The aqueous phase separated off is extracted twice with ethyl acetate; the organic phases are washed with satd NaHCO3 solution, and twice with water and brine, dried (MgSO4) and evaporated. Stirring the residue in diethyl ether yields 4-(3-chloroanilino)-6-[(4-methoxybenzylamino)-methyl]-7H-pyrrolo[2,3-d]pyrimidine; HPLC: tRet(Grad20)=9.5; TLC-Rf=0.17 (CH2Cl2/methanol=10:1); FAB-MS: (M+H)+=394.

Workup

  1. customis hydrogenated at RT and finally at 50° C
  2. filtrationThe catalyst is filtered off
  3. customthe filtrate is evaporated
  4. dissolutionthe residue is dissolved in ethyl acetate
  5. customThe aqueous phase separated off
  6. extractionis extracted twice with ethyl acetate
  7. washthe organic phases are washed with satd NaHCO3 solution
  8. dry with materialtwice with water and brine, dried (MgSO4)
  9. customevaporated

Sources & evidence

ORD record
ord-6a1fd1ff8b964d89a98a0bc8f300c2f6
Source dataset
uspto-grants-2001_01
Patent number
US06180636B2

Reaction notes

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