4-Chlorobenzaldehyde → HCID 178477972, compound

HRID 1397618Notes

Reaction equation

HRID 1397618 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH2:8])[C:3]=1[NH2:9].O1CCOCC1.[Cl:16][C:17]1[CH:24]=[CH:23][C:20]([CH:21]=O)=[CH:19][CH:18]=1>>[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[C:3]=1[N:9]=[C:21]([C:20]1[CH:23]=[CH:24][C:17]([Cl:16])=[CH:18][CH:19]=1)[NH:8]2

Participants

4

Reactant 3

HCID 77264-ChlorobenzaldehydeHCID 312751,4-DioxaneHCID 780104,5-Pyrimidinediamine, 6-chloro-

Product 1

HCID 178477972HCID 178477972, compound

Conditions

Temperature
100 °C

Procedure

To a solution of 6-Chloro-4,5-diaminopyrimidine (1 g, 0.007 mol) (Example 89, step a) in 1,4-Dioxane (60 mL, 0.8 mol) was added 4-Chlorobenzaldehyde (2.2 g, 0.016 mol) and Ferric chloride (2.5 g, 0.015 mol) mixed with 28.6 g silica gel, and the mixture was heated at 100° C. for 20 hours. The reaction was cooled to 23° C., filtered and washed with 10% ethanol/ethyl acetate and concentrated. The residue was dissolved in ethyl acetate and washed with water, brine, and concentrated. The residue was triturated in diethyl ether to obtain 272 mg (10%). LC/MS: Rt=1.54 min, ES+ 265 (AA standard).

Workup

  1. additionmixed with 28.6 g silica gel
  2. temperatureThe reaction was cooled to 23° C.
  3. filtrationfiltered
  4. washwashed with 10% ethanol/ethyl acetate
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved in ethyl acetate
  7. washwashed with water, brine
  8. concentrationconcentrated
  9. customThe residue was triturated in diethyl ether
  10. customto obtain 272 mg (10%)

Sources & evidence

ORD record
ord-4a32310a3e724a949f3609acf1268aa2
Source dataset
uspto-grants-2014_12
Patent number
US08901136B2

Reaction notes

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