4-(2-Bromo-1,3-thiazol-5-yl)-7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidine → 4-(2-Bromo-1,3-thiazol-5-yl)-7H-pyrrolo[2,3-d]pyrimidine

HRID 44939Notes

Reaction equation

HRID 44939 reaction equation
[Br:1][C:2]1[S:3][C:4]([C:7]2[C:8]3[CH:15]=[CH:14][N:13](COCC[Si](C)(C)C)[C:9]=3[N:10]=[CH:11][N:12]=2)=[CH:5][N:6]=1>C(Cl)Cl.C(O)(C(F)(F)F)=O>[Br:1][C:2]1[S:3][C:4]([C:7]2[C:8]3[CH:15]=[CH:14][NH:13][C:9]=3[N:10]=[CH:11][N:12]=2)=[CH:5][N:6]=1

Participants

4

Reactant 1

HCID 574776224-(2-Bromo-1,3-thiazol-5-yl)-7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 574776214-(2-Bromo-1,3-thiazol-5-yl)-7H-pyrrolo[2,3-d]pyrimidineYield 72%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 4-(2-bromo-1,3-thiazol-5-yl)-7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo-[2,3-d]pyrimidine (370 mg, 0.90 mmol) in DCM (5.0 mL) and TFA (1.0 mL) was stirred at room temperature for 7 hours. The mixture was then concentrated, re-dissolved in methanol (2 mL), and ethylenediamine (0.5 mL) was added. The mixture was stirred for 6 hours at room temperature. The mixture was diluted with DCM (10 mL), and the precipitate was isolated by filtration and washed with a small amount of DCM to afford desired product (182 mg, 72%).

Workup

  1. concentrationThe mixture was then concentrated
  2. dissolutionre-dissolved in methanol (2 mL)
  3. additionethylenediamine (0.5 mL) was added
  4. additionThe mixture was diluted with DCM (10 mL)
  5. customthe precipitate was isolated by filtration
  6. washwashed with a small amount of DCM

Sources & evidence

ORD record
ord-c1da49f60b54402bab917f975f0b70ac
Source dataset
uspto-grants-2013_09
Patent number
US08541425B2

Reaction notes

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