Isopropanol → HCID 178497917, compound

HRID 1884907Notes

Reaction equation

HRID 1884907 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4](Cl)[N:3]=1.[CH3:12][O:13][C:14](=[O:22])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([NH2:21])[CH:16]=1.C(O)(C)C>C(O)CCCC>[CH3:12][O:13][C:14](=[O:22])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([NH:21][C:4]2[N:3]=[C:2]([Cl:1])[N:10]=[C:9]3[C:5]=2[N:6]=[CH:7][NH:8]3)[CH:16]=1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 78274Benzoic acid, 3-amino-, methyl esterHCID 53244122,6-Dichloropurine

Product 1

HCID 178497917HCID 178497917, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 62761-PentanolSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of 2,6-dichloropurine (17 g, 90 mmol) in 300 ml of 1-pentanol are added 37.8 g (250 mmol) of methyl-3-aminobenzoate and stirred for 8 hours at 75° C. After cooling to RT, 200 ml of isopropanol is added and the mixture is stirred for 1 h. After filtration, the precipitate is taken up into MeOH/H2O and treated with NaHCO3 to pH >8. After filtration, the product ist washed with H2O and MeOH and dried to obtain 25.4 g (93% yield) of 3-(2-chloro-9H-purin-6-yl-amino)-benzoic acid methyl ester, Rf=0.5; (CH2Cl2/MeOH (9/1)); m.p. 242° C.; ESI-MS: 304 (M+H)+.

Workup

  1. temperatureAfter cooling to RT
  2. stirringthe mixture is stirred for 1 h
  3. filtrationAfter filtration
  4. additiontreated with NaHCO3 to pH >8
  5. filtrationAfter filtration
  6. washthe product ist washed with H2O and MeOH
  7. customdried

Sources & evidence

ORD record
ord-82a363fe765643f39d98ae801985fd40
Source dataset
uspto-grants-2004_07
Patent number
US06767906B2

Reaction notes

Loading…