Methanol → HCID 23282778, compound

HRID 369862Notes

Reaction equation

HRID 369862 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][CH:26]=1)[NH:5][C:6]1[C:7]2[CH:14]=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([C:21]([OH:23])=[O:22])=[CH:17][CH:16]=3)[NH:12][C:8]=2[N:9]=[CH:10][N:11]=1.S(=O)(=O)(O)O.[CH3:32]O>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][CH:26]=1)[NH:5][C:6]1[C:7]2[CH:14]=[C:13]([C:15]3[CH:16]=[CH:17][C:18]([C:21]([O:23][CH3:32])=[O:22])=[CH:19][CH:20]=3)[NH:12][C:8]=2[N:9]=[CH:10][N:11]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 23282681HCID 23282681, compound

Product 1

HCID 23282778HCID 23282778, compound

Procedure

0.5 g (1.37 mmol) of 4-(3-chloro-anilino)-6-(4-carboxy-phenyl)-7H-pyrrolo[2,3-d]-pyrimidine suspended in 100 ml of methanol is heated under reflux for 24 hours with 0.1 ml of concentrated sulfuric acid. The solution is concentrated and stirred in methanol/diethyl ether. The crystals are filtered off and then suspended in methanol/water. The suspension is adjusted to pH 7-8 with sodium hydrogen carbonate solution and stirred at RT for 30 min. The crystals are filtered off with suction, washed with water, methanol and diethyl ether and dried. The title compound is obtained in the form of colorless crystals, m.p.>300° C.; TLC-Rf =0.6 (toluene/ethyl acetate [3:7]); FAB-MS: (M+H)+ =378.

Workup

  1. temperatureis heated
  2. concentrationThe solution is concentrated
  3. filtrationThe crystals are filtered off
  4. stirringstirred at RT for 30 min
  5. filtrationThe crystals are filtered off with suction
  6. washwashed with water, methanol and diethyl ether
  7. customdried

Sources & evidence

ORD record
ord-01f33ec3ea66475e8a01dc2905cf20b4
Source dataset
uspto-grants-2000_10
Patent number
US06140332

Reaction notes

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