1-(2-Hydroxyethyl)piperazine → Methyl Hydroxyethyl Piperazinyl Methyl Pyrimidinylamino Thiazolecarboxylate

HRID 515253Notes

Reaction equation

HRID 515253 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1.Br[C:11]1[N:16]=[C:15]([CH3:17])[N:14]=[C:13]([NH:18][C:19]2[S:20][C:21]([C:24]([O:26][CH3:27])=[O:25])=[CH:22][N:23]=2)[CH:12]=1.CCN(C(C)C)C(C)C>C(O)CCC>[OH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][N:7]([C:11]2[N:16]=[C:15]([CH3:17])[N:14]=[C:13]([NH:18][C:19]3[S:20][C:21]([C:24]([O:26][CH3:27])=[O:25])=[CH:22][N:23]=3)[CH:12]=2)[CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 76771-(2-Hydroxyethyl)piperazine2×HCID 81531DiisopropylethylamineHCID 49821806Methyl 2-(6-bromo-2-methylpyrimidin-4-ylamino)thiazole-5-formate2×

Product 1

HCID 49821888Methyl Hydroxyethyl Piperazinyl Methyl Pyrimidinylamino ThiazolecarboxylateYield 83.8%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

1-(2-hydroxyethyl)piperazine (Compound 3) (65 g, 0.5 mol), methyl 2-(6-bromo-2-methylpyrimidin-4-ylamino)thiazole-5-formate (Compound 11) (32.9 g, 0.1 mol), n-butanol (280 mL) and DIPEA (28.3 g, 0.2 mol) were mixed in reaction flask and reacted by refluxing for 8 h. Cooled down to room temperature and crystals precipitated overnight. After air pump filtration the cake was rinsed by n-butanol and dried to give target Compound 6 (31.7 g, yield: 83.8%).

Workup

  1. customreacted
  2. temperatureby refluxing for 8 h
  3. customcrystals precipitated overnight
  4. filtrationAfter air pump filtration the cake
  5. washwas rinsed by n-butanol
  6. customdried

Sources & evidence

ORD record
ord-551643eec42c4952b18867e46e3c7ce9
Source dataset
uspto-grants-2015_08
Patent number
US09108954B2

Reaction notes

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