Sodium hydride → [4-(2-Ethyl-5,7-dimethyl-pyrazolo[1,5-a]pyrimidin-3-ylmethyl)-phenoxy]-acetic acid methyl ester

HRID 403486Notes

Reaction equation

HRID 403486 reaction equation
[CH2:1]([C:3]1[C:13]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)=[C:6]2[N:7]=[C:8]([CH3:12])[CH:9]=[C:10]([CH3:11])[N:5]2[N:4]=1)[CH3:2].[H-].[Na+].Br[CH2:25][C:26]([O:28][CH3:29])=[O:27]>C1COCC1>[CH3:29][O:28][C:26](=[O:27])[CH2:25][O:21][C:18]1[CH:17]=[CH:16][C:15]([CH2:14][C:13]2[C:3]([CH2:1][CH3:2])=[N:4][N:5]3[C:10]([CH3:11])=[CH:9][C:8]([CH3:12])=[N:7][C:6]=23)=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 683792244-((2-Ethyl-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)methyl)phenol

Product 1

HCID 68379074[4-(2-Ethyl-5,7-dimethyl-pyrazolo[1,5-a]pyrimidin-3-ylmethyl)-phenoxy]-acetic acid methyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(2-Ethyl-5,7-dimethyl-pyrazolo[1,5-a]pyrimidin-3-ylmethyl)-phenol (8) (1 g, 3.55 mmol) was dissolved in 30 ml of THF and after addition of NaH (60% in mineral oil, 0.171 g, 4.27 mmol) the mixture was stirred for 20 min at rt. Then methyl 2-bromoacetate (0.382 ml, 3.91 mmol) was added and the mixture was stirred for 16 h at rt. The mixture was quenched with H2O. The mixture was concentrated. The residue was diluted with ethyl acetate, washed with water and NaCl-solution, dried over Na2 SO4 and evaporated. The crude product was used in the next step without further purification.

Workup

  1. stirringthe mixture was stirred for 16 h at rt
  2. customThe mixture was quenched with H2O
  3. concentrationThe mixture was concentrated
  4. additionThe residue was diluted with ethyl acetate
  5. washwashed with water and NaCl-solution
  6. customdried over Na2 SO4
  7. customevaporated
  8. customThe crude product was used in the next step without further purification

Sources & evidence

ORD record
ord-d3ae75602a5c4dd29d2f117d2335bfb5
Source dataset
uspto-grants-2014_06
Patent number
US08748435B2

Reaction notes

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