Sodium hydride → HCID 69486753, compound

HRID 498246Notes

Reaction equation

HRID 498246 reaction equation
CO[C:3](=[O:20])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[CH:15]=[C:14]([CH3:16])[N:13]=[C:12]([N:17]([CH3:19])[CH3:18])[N:11]=2)[CH:5]=1.[H-].[Na+].Cl.CNC(N)=N.O=C(C)CC(C1C=[C:36](C=CC=1)[C:37]([OH:39])=[O:38])=O>CC(O)C.O>[C:4]([O:39][C:37](=[O:38])[CH2:36][C:3]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[CH:15]=[C:14]([CH3:16])[N:13]=[C:12]([N:17]([CH3:18])[CH3:19])[N:11]=2)[CH:5]=1)=[O:20])([CH3:9])([CH3:5])[CH3:3]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 22317858HCID 22317858, compoundHCID 69486708HCID 69486708, compoundHCID 178485118HCID 178485118, compound

Product 1

HCID 69486753HCID 69486753, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
50 °C

Procedure

The title compound was prepared from 3-(2-dimethylamino-6-methyl-pyrimidin-4-yl)-benzoic acid methyl ester [prepared by the following procedure: A mixture of NaH (50% dispersion in mineral oil, 1.56 g, 32.5 mmol) in 2-propanol (45 ml) was stirred at 50° C. for 10 min. N-methylguanidine hydrochloride (3.3 g, 30 mmol) was added and stirring was continued for 10 min. After the addition of 3-(3-oxo-butyryl)-benzoic acid (3.1 g, 15 mmol), the mixture was stirred at 80° C. for 48 h. After cooling to RT, H2O (100 ml) was added and the mixture was concentrated in vacuum to a volume of ca. 80 ml. The pH was set to 2.5 with 25% HCl and the precipitate was collected, dried and then esterified by stirring in 1N HCl-MeOH (30 ml) for 60 h at RT The crude product was purified by chromatography (silica gel, AcOEt) to give the methyl ester as light yellow solid (0.27 g).] (0.26 g, 1 mmol) by treatment with lithium tert-butyl acetate according to general procedure K (method b). Obtained as a light yellow oil (0.38 g, crude product).

Workup

  1. customprepared by the following procedure
  2. stirringstirring
  3. waitwas continued for 10 min
  4. stirringthe mixture was stirred at 80° C. for 48 h
  5. temperatureAfter cooling to RT
  6. concentrationthe mixture was concentrated in vacuum to a volume of ca. 80 ml
  7. customthe precipitate was collected
  8. customdried
  9. stirringby stirring in 1N HCl-MeOH (30 ml) for 60 h at RT The crude product
  10. customwas purified by chromatography (silica gel, AcOEt)

Sources & evidence

ORD record
ord-2d80dee2da614cb881f56f217cd842ea
Source dataset
uspto-grants-2005_09
Patent number
US06949542B2

Reaction notes

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