4-Chloro-2-(methylthio)pyrimidine-5-carboxylic acid ethyl ester → HCID 9151271, compound

HRID 1883544Notes

Reaction equation

HRID 1883544 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7](Cl)=[N:8][C:9]([S:12][CH3:13])=[N:10][CH:11]=1)=[O:5])[CH3:2].[NH2:15][C:16]1[CH:24]=[C:23]2[C:19]([CH:20]=[N:21][NH:22]2)=[CH:18][CH:17]=1.C(N(CC)C(C)C)(C)C>CO>[CH2:1]([O:3][C:4]([C:6]1[C:7]([NH:15][C:16]2[CH:24]=[C:23]3[C:19]([CH:20]=[N:21][NH:22]3)=[CH:18][CH:17]=2)=[N:8][C:9]([S:12][CH3:13])=[N:10][CH:11]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 800084-Chloro-2-(methylthio)pyrimidine-5-carboxylic acid ethyl esterHCID 814231H-Indazol-6-amineHCID 81531Diisopropylethylamine

Product 1

HCID 9151271HCID 9151271, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

To the solution of 4-chloro-2-methylthio-5-pyrimidine carboxylic acid ethyl ester (5 g) and 6-aminoindazole (3.15 g) in methanol (70 ml) was added N,N-diisopropylethylamine (4.2 ml), and then the solution was reacted at 30-35° C. for 4 hr. The reaction mixture was cooled, and then stirred at 20° C. for 1 hr. The reaction mixture was filtered, washed with methanol (20 ml) and dried at 40-50° C. in vacuo to obtain the desired compound (5.8 g, 82%).

Workup

  1. customthe solution was reacted at 30-35° C. for 4 hr
  2. temperatureThe reaction mixture was cooled
  3. filtrationThe reaction mixture was filtered
  4. washwashed with methanol (20 ml)
  5. customdried at 40-50° C. in vacuo

Sources & evidence

ORD record
ord-ff85c97a14494cdd87612b8f76e83792
Source dataset
uspto-grants-2004_07
Patent number
US06762189B1

Reaction notes

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