p-Toluenesulfonic acid → HCID 19012212, compound

HRID 466699

Reaction equation

HRID 466699 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([NH2:9])=[C:4]([CH3:10])[N:3]=1.CO[C:13](OC)(OC)[CH2:14][CH2:15][CH3:16].CC1C=CC(S(O)(=O)=O)=CC=1>COCCO>[Cl:1][C:2]1[N:7]=[C:6]2[C:5]([NH:9][C:13]([CH2:14][CH2:15][CH3:16])=[N:8]2)=[C:4]([CH3:10])[N:3]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 1235121,1,1-TrimethoxybutaneHCID 2752952-Chloro-4,5-diamino-6-methylpyrimidine

Product 1

HCID 19012212HCID 19012212, compoundYield 47.1%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 2-Chloro-4,5-diamino-6-methylpyrimidine (0.80 g, 5.04 mmol), trimethylorthobutyrate (1.2 ml, 7.6 mmol) and p-TsOH (0.08 g) in 2-methoxyethanol (24 ml) was heated in an oil bath at 140° C. for 24 hours. The product was isolated as described in Step 2 of Example 12 and purified by flash chromatography using EtOAc-hexane (1:1) to give the crystalline titled compound (0.5 g, 47%).

Workup

  1. customThe product was isolated
  2. custompurified by flash chromatography

Sources & evidence

ORD record
ord-889a2aec602c401a8cdf19bffb69e9b2
Source dataset
uspto-grants-1992_10
Patent number
US05157026

Linked notes

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