Sodium hydride → HCID 57936191, compound

HRID 1434933Notes

Reaction equation

HRID 1434933 reaction equation
[CH3:1][S:2][C:3]1[N:8]=[C:7]([C:9]2[CH:13]=[CH:12][NH:11][CH:10]=2)[CH:6]=[CH:5][N:4]=1.[H-].[Na+].[CH3:16][O:17][C:18](=[O:22])[CH2:19][CH2:20]Br>C1COCC1>[CH3:16][O:17][C:18](=[O:22])[CH2:19][CH2:20][N:11]1[CH:12]=[CH:13][C:9]([C:7]2[CH:6]=[CH:5][N:4]=[C:3]([S:2][CH3:1])[N:8]=2)=[CH:10]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 76934Methyl 3-bromopropanoateHCID 57936139HCID 57936139, compound

Product 1

HCID 57936191HCID 57936191, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

2-Methylsulfanyl-4-(1H-pyrrol-3-yl)-pyrimidine (260 mg, 1.36 mmol) was added to a suspension of fat free sodium hydride (39 mg, 1.63 mmol) in 5 ml of THF. The mixture was heated to 50° C. for 20 minutes. Then, 3-bromo-propionic acid methyl ester (0.156 ml, 1.36 mmol) was added and the temperature was increased to 80° C. After 14 hours, the mixture was cooled, quenched with water and extracted with ether. The combined organic layers were washed with brine, dried over sodium sulfate and evaporated. The crude product was used without further purification. Yield: 302 mg (80%).

Workup

  1. temperaturethe temperature was increased to 80° C
  2. temperaturethe mixture was cooled
  3. customquenched with water
  4. extractionextracted with ether
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated
  8. customThe crude product was used without further purification

Sources & evidence

ORD record
ord-64d0d13ab2b8417f81204d01f2272360
Source dataset
uspto-grants-2009_11
Patent number
US07615562B2

Reaction notes

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