Sodium hydride → HCID 69559023, compound

HRID 1934422Notes

Reaction equation

HRID 1934422 reaction equation
[H-].[Na+].[C:3]([O:7][CH3:8])(=[O:6])[CH2:4][OH:5].[CH3:9][C:10]1[N:11]=[C:12](Cl)[C:13]2[CH:18]=[C:17]([CH2:19][CH3:20])[N:16]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:14]=2[N:15]=1.CCCCCCC.C(OCC)(=O)C>C1C=CC=CC=1>[CH3:8][O:7][C:3](=[O:6])[CH2:4][O:5][C:12]1[C:13]2[CH:18]=[C:17]([CH2:19][CH3:20])[N:16]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:14]=2[N:15]=[C:10]([CH3:9])[N:11]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 66774Methyl GlycolateHCID 21899848Ethylacetate heptaneHCID 22466480HCID 22466480, compound

Product 1

HCID 69559023HCID 69559023, compoundYield 62.6%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
60 °C

Procedure

To a suspension of 240 mg (10.0 mmol) of sodium hydride in 15 mL of benzene was added 783 mg (8.69 mmol) of methyl glycolate and 1.91 g (6.68 mmol) of 2-methyl-4-chloro-6-ethyl-7-(phenylmethyl)-7H-pyrrolo[2,3-d]pyrimidine. The mixture was heated at 60° C. and monitored by TLC (silica, 7:3 heptane-ethyl acetate) for conversion to product. After 5 days the reaction was cooled to ambient temperature and partitioned by the addition of 10 mL of 2 M sodium hydrogen sulfate and 30 mL of ethyl acetate. The aqueous phase was extracted with 10 mL of ethyl acetate. The combined organic phases were dried with sodium sulfate and concentrated to 2.5 g of oil. The residue was purified by flash chromatography (200 g silica, 7:3 heptane-ethyl acetate) to provide 1.42 g (62%) of [[2-methyl-6-ethyl-7-(phenylmethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]acetic acid methyl ester as a white solid. nmr (500 MHz, CDCl3) δ1.27 (t, J=7.4 Hz, 3H), 2.57 (q, J=7.4 Hz, 2H), 2.60 (s, 3H), 3.80 (s, 3H), 5.08 (s, 2H), 5.44 (s, 2H), 6.34 (s, 1H), 7.02 (d, J=7.1 Hz, 2H), 7.25 (m, 3H)

Workup

  1. temperatureAfter 5 days the reaction was cooled to ambient temperature
  2. custompartitioned by the addition of 10 mL of 2 M sodium hydrogen sulfate and 30 mL of ethyl acetate
  3. extractionThe aqueous phase was extracted with 10 mL of ethyl acetate
  4. dry with materialThe combined organic phases were dried with sodium sulfate
  5. concentrationconcentrated to 2.5 g of oil
  6. customThe residue was purified by flash chromatography (200 g silica, 7:3 heptane-ethyl acetate)

Sources & evidence

ORD record
ord-32ade74f4aaf4f459adc7be58400f07a
Source dataset
uspto-grants-2002_05
Patent number
US06384041B1

Reaction notes

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