Sodium hydride → HCID 22466488, compound

HRID 1934433Notes

Reaction equation

HRID 1934433 reaction equation
[CH3:1][S:2][C:3]1[NH:8][C:7]2=[N:9][C:10]([CH2:12][CH3:13])=[CH:11][C:6]2=[C:5]([Cl:14])[N:4]=1.[F:15][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=1)[CH2:19]Br.[H-].[Na+]>O1CCCC1>[CH3:1][S:2][C:3]1[N:4]=[C:5]([Cl:14])[C:6]2[CH:11]=[C:10]([CH2:12][CH3:13])[N:9]([CH2:19][C:18]3[CH:21]=[CH:22][CH:23]=[C:16]([F:15])[CH:17]=3)[C:7]=2[N:8]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 680073-Fluorobenzyl bromideHCID 178435386HCID 178435386, compound

Product 1

HCID 22466488HCID 22466488, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 300 mg (1.31 mmol) of 2-(methylthio)-4-chloro-6-ethyl-1H-pyrrolo[2,3-d]pyrimidine in 10 mL of tetrahydrofuran (THF) was added to a 0° C. slurry of 377 mg (1.97 mmol) of 3-fluorobenzyl bromide and 55 mg (2.30 mmol) of sodium hydride in 10 mL of THF. The reaction was allowed to warm to ambient temperature and stirred for 16 hours. The reaction was quenched by the addition of 15 mL of brine. The organic phase was dried with sodium sulfate and concentrated to an oil. The product precipitated upon addition of hexanes to provide 384 mg (87%) of 2-(methylthio)-4-chloro-6-ethyl-7-[(3-fluorophenyl)methyl]-7H-pyrrolo[2,3-d]pyrimidine as a light tan solid. nmr (300 MHz, CDCl3) δ1.11 (t, 3H), 2.58 (s, 3H), 2.59 (q, 2H), 5.39 (s, 2H), 6.29 (s, 1H), 6.75 (d, 1H), 6.85 (d, 1H), 6.96 (dt, 1H), 7.26 (dt, 1H)

Workup

  1. customThe reaction was quenched by the addition of 15 mL of brine
  2. dry with materialThe organic phase was dried with sodium sulfate
  3. concentrationconcentrated to an oil
  4. customThe product precipitated upon addition of hexanes

Sources & evidence

ORD record
ord-9e7bea11793f4defa9709666104ab519
Source dataset
uspto-grants-2002_05
Patent number
US06384041B1

Reaction notes

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