Ammonium Chloride → 7H-Pyrrolo[2,3-d]pyrimidine-5-carbonitrile

HRID 1025616Notes

Reaction equation

HRID 1025616 reaction equation
S([N:11]1[C:15]2[N:16]=[CH:17][N:18]=[CH:19][C:14]=2[C:13]([C:20]#[N:21])=[CH:12]1)(C1C=CC(C)=CC=1)(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC.[F-].[NH4+].[Cl-]>O1CCCC1>[N:16]1[C:15]2[NH:11][CH:12]=[C:13]([C:20]#[N:21])[C:14]=2[CH:19]=[N:18][CH:17]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 710084747-tosyl-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

Product 1

HCID 226052697H-Pyrrolo[2,3-d]pyrimidine-5-carbonitrileYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a 15 mL round-bottomed flask, 7-tosyl-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile (1 g, 3.35 mmol, Eq: 1.00) and TBAF (13.4 ml, 13.4 mmol, Eq: 4.00) were combined with Tetrahydrofuran to give an off-white solution. The reaction mixture was stirred for 3 h. The reaction mixture was poured into 20 mL sat NH4Cl and extracted with EtOAc (3×25 mL). The organic layers were dried over MgSO4 and concentrated in vacuo. The crude material was triturated with diethyl ether (1×20 mL) to obtain 7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile (312 mg, 65%).

Workup

  1. customto give an off-white solution
  2. additionThe reaction mixture was poured into 20 mL
  3. extractionextracted with EtOAc (3×25 mL)
  4. dry with materialThe organic layers were dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe crude material was triturated with diethyl ether (1×20 mL)

Sources & evidence

ORD record
ord-efb97f321be74879bc6e2d9a01d68d17
Source dataset
uspto-grants-2014_05
Patent number
US08729078B2

Reaction notes

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