p-Toluenesulfonic acid → HCID 19012216, compound

HRID 1029558Notes

Reaction equation

HRID 1029558 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH2:8])[C:3]=1[NH2:9].CO[C:12](OC)(OC)[CH2:13][CH2:14][CH2:15][CH3:16].CC1C=CC(S(O)(=O)=O)=CC=1>COCCO>[CH2:13]([C:12]1[NH:9][C:3]2[C:4](=[N:5][CH:6]=[N:7][C:2]=2[Cl:1])[N:8]=1)[CH2:14][CH2:15][CH3:16]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 780104,5-Pyrimidinediamine, 6-chloro-HCID 83755Trimethyl orthovalerate

Product 1

HCID 19012216HCID 19012216, compoundYield 26.8%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

A mixture of 6-Chloro-4,5-diaminopyrimidine (0.289 g, 2 mmol) (from Step 1 of Example 12), trimethylorthovalerate (0.52 ml, 3 mmol) and p-TsOH (0.04 g) in 2-methoxyethanol (10 ml) was refluxed for 24 hours. The product was isolated and purified as described in Step 2 of Example 12 to give the crystalline titled compound (0.113 g, 23%). NMR (CDCl3): δ0.997 (t, J=9 Hz, 3H), 1.484 (m, 2H), 1.925 (m, 2H), 3.075 (m, 2H), 7.27 (s, 1H) and 8.723 (s, 1H). FAB-MS: m/e 211 and 213 (M+H). Analysis calculated for C9H11N4Cl: C, 51.31; H, 5.26; N, 26.60. Found: C, 51.34; H, 5.30, N, 26.46.

Workup

  1. temperaturewas refluxed for 24 hours
  2. customThe product was isolated
  3. custompurified

Sources & evidence

ORD record
ord-43c4a0aa77624be083bb3fd5f284738e
Source dataset
uspto-grants-1992_04
Patent number
US05102880

Reaction notes

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