Potassium Carbonate → 4-(1H-pyrrolo[3,2-c]pyridin-3-yl)-N-o-tolylpyrimidin-2-amine

HRID 1042552Notes

Reaction equation

HRID 1042552 reaction equation
C(=O)([O-])[O-].[K+].[K+].C[Si](C)(C)[C:9]#[C:10][C:11]([C:13]1[C:17]2[CH:18]=[N:19][CH:20]=[CH:21][C:16]=2[N:15](C(OC(C)(C)C)=O)[CH:14]=1)=O.[N+]([O-])([O-])=O.[CH3:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[NH:42][C:43]([NH2:45])=[NH2+:44]>COCCO>[NH:15]1[C:16]2[CH:21]=[CH:20][N:19]=[CH:18][C:17]=2[C:13]([C:11]2[CH:10]=[CH:9][N:45]=[C:43]([NH:42][C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=3[CH3:35])[N:44]=2)=[CH:14]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 58230463Tert-butyl 3-(3-trimethylsilylpropynoyl)pyrrolo[3,2-c]pyridine-1-carboxylateHCID 178424377HCID 178424377, compound

Product 1

HCID 249923864-(1H-pyrrolo[3,2-c]pyridin-3-yl)-N-o-tolylpyrimidin-2-amine

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

173 mg (1.25 mmol) of potassium carbonate are added to a solution of 171 mg (0.50 mmol) of tert-butyl 3-(3-trimethylsilylpropynoyl)pyrrolo[3,2-c]pyridine-1-carboxylate and 265 mg (1.25 mmol) of 2-methylphenylguanidinium nitrate (prepared by the method of J. L. Hughes et al., J. Med. Chem. 1975, 18, 1077-1088) in 2.5 ml of ethylene glycol monomethyl ether, and the mixture is heated at the boil for 18 hours. After cooling, the reaction mixture is partitioned between water and dichloromethane. The organic phase is dried over sodium sulfate and evaporated. The residue is chromatographed on a silica-gel column with dichloromethane/methanol as eluent, giving [4-(1H-pyrrolo-[3,2-c]pyridin-3-yl)pyrimidin-2-yl]-o-tolyl-amine (“A6”) as beige crystals; ESI 303;

Workup

  1. customprepared by the method of J
  2. temperatureAfter cooling
  3. customthe reaction mixture is partitioned between water and dichloromethane
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. customevaporated
  6. customThe residue is chromatographed on a silica-gel column with dichloromethane/methanol as eluent

Sources & evidence

ORD record
ord-14a87e84c53744d3abdcdf1b6d1689a6
Source dataset
uspto-grants-2013_10
Patent number
US08557977B2

Reaction notes

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