Ethanesulfonic acid → 6-chloro-9-(4-chlorophenyl)-8-ethyl-9H-purine

HRID 1626314

Reaction equation

HRID 1626314 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)[C:3]=1[NH2:16].[C:17](OCC)(OCC)(OCC)[CH2:18][CH3:19].C(S(O)(=O)=O)C>>[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[C:3]=1[N:16]=[C:17]([CH2:18][CH3:19])[N:8]2[C:9]1[CH:10]=[CH:11][C:12]([Cl:15])=[CH:13][CH:14]=1

Participants

4

Reactant 3

HCID 11668Ethanesulfonic acidHCID 66995Ethyl orthopropionateHCID 167263116-Chloro-N4-(4-chlorophenyl)pyrimidine-4,5-diamine

Product 1

HCID 866706316-chloro-9-(4-chlorophenyl)-8-ethyl-9H-purineYield 81%

Procedure

6-chloro-N4-(4-chlorophenyl)pyrimidine-4,5-diamine obtained in step 1 (1.5 g, 5.88 mmol) was dissolved in triethyl ortho propionate (11.8 ml, 58.8 mmol) at room temperature. Ethanesulfonic acid (0.48 mL, 5.88 mmol) was added slowly to the resulting solution at 0 r and warmed to room temperature. The reaction mixture thus obtained was stirred for 6 hours at 50° C. The resulting mixture was filtered with NaHCO3(aq)/H2O. The collected solid was dried under reduced pressure to obtain the title compound (1.39 g, 81%) as white solid.

Workup

  1. customThe reaction mixture thus obtained
  2. filtrationThe resulting mixture was filtered with NaHCO3(aq)/H2O
  3. customThe collected solid was dried under reduced pressure

Sources & evidence

ORD record
ord-9001c1498316440a8c36d30f3dd9cb14
Source dataset
uspto-grants-2014_07
Patent number
US08785453B2

Linked notes

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