Benzyl Bromide → HCID 22466480, compound

HRID 1934419Notes

Reaction equation

HRID 1934419 reaction equation
[CH3:1][C:2]1[NH:7][C:6]2=[N:8][C:9]([CH2:11][CH3:12])=[CH:10][C:5]2=[C:4]([Cl:13])[N:3]=1.[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[H-].[Na+]>O1CCCC1>[CH3:1][C:2]1[N:3]=[C:4]([Cl:13])[C:5]2[CH:10]=[C:9]([CH2:11][CH3:12])[N:8]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 178435384HCID 178435384, compound

Product 1

HCID 22466480HCID 22466480, compoundYield 67.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 500 mg (2.55 mmol) of 2-methyl-4-chloro-6-ethyl-1H-pyrrolo[2,3-d]pyrimidine in 5.0 mL of tetrahydrofuran (THF) was added to a 2° C. slurry of 437 mg (2.55 mmol) of benzylbromide and 60 mg (2.55 mmol) of sodium hydride in 4.0 mL of THF. The reaction was allowed to warm to ambient temperature and stirred for 18 hours. The reaction was quenched by the addition of 7 mL of 2 M sodium hydrogen sulfate and then extracted with 7 mL of ethyl acetate. The organic phase was dried with sodium sulfate and concentrated to 500 mg. The residue was purified by flash chromatography (50 g of silica gel, methylene chloride) to provide 490 mg (67%) of 2-methyl-4-chloro-6-ethyl-7-(phenylmethyl)-7H-pyrrolo[2,3-d]pyrimidine as a solid. nmr (500 MHz, CDCl3) δ1.29 (t, J=7.5 Hz, 3H), 2.61 (q, J=7.5 Hz, 2H), 2.74 (s, 3H), 5.45 (s, 2H), 6.33 (s, 1H), 7.03 (d, J=7.0 Hz, 2H), 7.28 (m, 3H)

Workup

  1. customThe reaction was quenched by the addition of 7 mL of 2 M sodium hydrogen sulfate
  2. extractionextracted with 7 mL of ethyl acetate
  3. dry with materialThe organic phase was dried with sodium sulfate
  4. concentrationconcentrated to 500 mg
  5. customThe residue was purified by flash chromatography (50 g of silica gel, methylene chloride)

Sources & evidence

ORD record
ord-b2c805381b0b44f3be3a7ebc49942d4d
Source dataset
uspto-grants-2002_05
Patent number
US06384041B1

Reaction notes

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