Methyl formate → Methyl 3-hydroxy-2-((2-methoxypyrimidin-5-yl)methyl)acrylate

HRID 705792Notes

Reaction equation

HRID 705792 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[N:10]=[CH:9][C:8]([CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])=[CH:7][N:6]=1.[CH:17](OC)=[O:18]>COCCOC>[CH3:16][O:15][C:13](=[O:14])[C:12]([CH2:11][C:8]1[CH:9]=[N:10][C:5]([O:4][CH3:3])=[N:6][CH:7]=1)=[CH:17][OH:18]

Participants

5

Reactant 3

HCID 7865Methyl formateHCID 24758Sodium hydrideHCID 67776226Methyl 3-[2-(methyloxy)-5-pyrimidinyl]propanoate

Product 1

HCID 67773588Methyl 3-hydroxy-2-((2-methoxypyrimidin-5-yl)methyl)acrylateYield 67.9%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

To a suspension of NaH (14.7 g, 367 mmol) in DME (216 mL) was added dropwise a mixture of methyl 3-[2-(methyloxy)-5-pyrimidinyl]propanoate (18 g, 92 mmol) and methyl formate (33.1 g, 550 mmol) in DME (216 mL) under N2 at 0° C. The reaction mixture was stirred at 25° C. overnight, then filtered through a pad of Celite. The filtrate was diluted with ether (500 mL), kept standing for about 2 h and re-filtered. The filtrated cake was washed with diethyl ether and dried to give the title compound (14 g, 51.7%), which was used into next step without further purification.

Workup

  1. additionwas added dropwise
  2. filtrationfiltered through a pad of Celite
  3. additionThe filtrate was diluted with ether (500 mL)
  4. waitkept standing for about 2 h
  5. filtrationre-filtered
  6. washThe filtrated cake was washed with diethyl ether
  7. customdried

Sources & evidence

ORD record
ord-06aa3a01a4c1417980707b3ab8883cdc
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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