Propanal → HCID 49819035, compound

HRID 2276291Notes

Reaction equation

HRID 2276291 reaction equation
[NH2:1][C:2]1[C:3]([N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)=[N:4][C:5]([S:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[N:6][C:7]=1[NH:8][CH3:9].[CH:26](=O)[CH2:27]C.[CH3:30]O>>[CH2:26]([C:9]1[N:8]([CH3:30])[C:7]2[C:2]([N:1]=1)=[C:3]([N:20]1[CH2:21][CH2:22][O:23][CH2:24][CH2:25]1)[N:4]=[C:5]([S:10][CH2:11][C:12]1[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=1)[N:6]=2)[CH3:27]

Participants

4

Reactant 3

HCID 527PropanalHCID 887MethanolHCID 11617472HCID 11617472, compound

Product 1

HCID 49819035HCID 49819035, compoundYield 80%

Procedure

5-amino-2-(4-methoxybenzylsulfanyl)-6-methylamino-4-morpholinopyrimidine (693 mg, 1.91 mmol) was dissolved in methanol (20 ml), propionaldehyde (2.76 ml, 38.3 mmol) was added and stirred at room temperature for 3 hours. The solvent was distilled away under reduced pressure, water was added and extracted twice with ethyl acetate. After combining the organic layers and washing with a saturated saline solution, it was dried with MgSO4 and the solvent was distilled away under reduced pressure. Separation and purification were performed by silica gel column chromatography (ethyl acetate:hexane=1:1) to obtain 610 mg (80% yield) of 8-ethyl-2-(4-methoxybenzylsulfanyl)-9-methyl-6-morpholino-9H-purine.

Workup

  1. distillationThe solvent was distilled away under reduced pressure, water
  2. additionwas added
  3. extractionextracted twice with ethyl acetate
  4. washwashing with a saturated saline solution, it
  5. dry with materialwas dried with MgSO4
  6. distillationthe solvent was distilled away under reduced pressure
  7. customSeparation and purification

Sources & evidence

ORD record
ord-8942f2f0709e4db692f30ec4e3ba4e1d
Source dataset
uspto-grants-2015_09
Patent number
US09132130B2

Reaction notes

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