4-Pyridinecarboxaldehyde → HCID 58442021, compound

HRID 552110Notes

Reaction equation

HRID 552110 reaction equation
[CH:1]1([NH:4][C:5]2[C:10]([NH2:11])=[CH:9][N:8]=[C:7]([NH:12][CH2:13][CH2:14][C:15]3[S:16][CH:17]=[CH:18][CH:19]=3)[N:6]=2)[CH2:3][CH2:2]1.[N:20]1[CH:25]=[CH:24][C:23]([CH:26]=O)=[CH:22][CH:21]=1>CC(N(C)C)=O>[CH:1]1([N:4]2[C:26]([C:23]3[CH:24]=[CH:25][N:20]=[CH:21][CH:22]=3)=[N:11][C:10]3[C:5]2=[N:6][C:7]([NH:12][CH2:13][CH2:14][C:15]2[S:16][CH:17]=[CH:18][CH:19]=2)=[N:8][CH:9]=3)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 133894-PyridinecarboxaldehydeHCID 58441956HCID 58441956, compound

Product 1

HCID 58442021HCID 58442021, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of 0.032 g (0.12 mmol, 1.0 eq.) of N4-cyclopropyl-N2-(2-(thiophen-2-yl)ethyl)pyrimidine-2,4,5-triamine (I-3) in 5 mL of DMA was added 0.05 mL (0.38 mmol, 3.2 eq.) of 4-pyridinecarboxaldehyde. The mixture was stirred at 140° C. for 16 h and the solvent was removed in vacuo. The residue was purified by flash chromatography (EtOAc) to afford 0.015 g (0.04 mmol, 35%) of 9-cyclopropyl-8-(pyridin-4-yl)-N-(2-(thiophen-2-yl)ethyl)-9H-purin-2-amine (I-4) as a yellow solid.

Workup

  1. customthe solvent was removed in vacuo
  2. customThe residue was purified by flash chromatography (EtOAc)

Sources & evidence

ORD record
ord-2e15963622534e3d87876a4f2d0da009
Source dataset
uspto-grants-2011_05
Patent number
US07951803B2

Reaction notes

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