2-(Methylamino)ethanol → HCID 505747, compound

HRID 1883550Notes

Reaction equation

HRID 1883550 reaction equation
S(Cl)(Cl)=O.C(O[C:8]([C:10]1[C:11]([NH:18][C:19]2[CH:20]=[C:21]3[C:25](=[CH:26][CH:27]=2)[NH:24][N:23]=[CH:22]3)=[N:12][C:13]([S:16][CH3:17])=[N:14][CH:15]=1)=[O:9])C.[CH3:28][NH:29][CH2:30][CH2:31][OH:32].[OH-].[Na+]>CO.O.CN(C)C=O.C(Cl)Cl>[OH:32][CH2:31][CH2:30][N:29]([CH3:28])[C:8]([C:10]1[C:11]([NH:18][C:19]2[CH:20]=[C:21]3[C:25](=[CH:26][CH:27]=2)[NH:24][N:23]=[CH:22]3)=[N:12][C:13]([S:16][CH3:17])=[N:14][CH:15]=1)=[O:9]

Participants

9

Reactant 4

HCID 80162-(Methylamino)ethanolHCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 11209679HCID 11209679, compound

Product 1

HCID 505747HCID 505747, compoundYield 45%

Reagents, catalysts & solvents 4

HCID 887MethanolSolvent2×HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To the solution of methylene chloride (120 ml) was added N,N-dimethylformamide (1.1 ml) and thionyl chloride (1.2 ml) and refluxed for 2 hr. The solution was added 4-(1H-5-indazolylamino)-2-methylthio-5-pyrimidinecarboxylic acid ethyl ester (3 g) prepared from preparation example 3, and refluxed for 10 hr. The reaction mixture was cooled and slowly added 2-(methylamino)ethanol (4 ml) at 0˜5° C. and stirred for 1 hr. The reaction mixture was added methanol (80 ml), stirred 5 min. and then filtered for removing impurity. The filtrate was concentration by evaporation under pressure and it was obtained a solid product. The solid product in methanol: H2O=1:1 was added aq. 3N NaOH (3 ml), stirred for 1 hr, filtered and washed with H2O. The desired compound (1.61 g. 45%) was obtained by recrystallization with methylene chloride:isopropyl ether=1:4.

Workup

  1. temperaturerefluxed for 2 hr
  2. customprepared from preparation example 3
  3. temperaturerefluxed for 10 hr
  4. temperatureThe reaction mixture was cooled
  5. filtrationfiltered
  6. customfor removing impurity
  7. concentrationconcentration
  8. customby evaporation under pressure
  9. customit was obtained a solid product
  10. stirringstirred for 1 hr
  11. filtrationfiltered
  12. washwashed with H2O

Sources & evidence

ORD record
ord-c5398f65c97445caaa4ab23543c67ca1
Source dataset
uspto-grants-2004_07
Patent number
US06762189B1

Reaction notes

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