Dimethylformamide → 4-Chloro-7H-pyrrolo(2,3-d)pyrimidine-5-carboxamide

HRID 1396602Notes

Reaction equation

HRID 1396602 reaction equation
[Cl:1][C:2]1[C:3]2[C:10]([C:11]([OH:13])=O)=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.C[N:15](C=O)C.C(Cl)(=O)C(Cl)=O>C(Cl)Cl.C1COCC1>[Cl:1][C:2]1[C:3]2[C:10]([C:11]([NH2:15])=[O:13])=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 224608664-Chloro-7H-pyrrolo(2,3-d)pyrimidine-5-carboxylic acid

Product 1

HCID 593610044-Chloro-7H-pyrrolo(2,3-d)pyrimidine-5-carboxamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylic acid (H-1) (3.11 g, 15.7 mmol, 1.0 eq) and a catalytic amount of DMF in a mixture of DCM (40 mL) and THF (40 mL) at RT, oxalyl chloride (2.0 mL, 23.5 mmol, 1.5 eq) is added dropwise. The resulting mixture is stirred for 2 h and then concentrated in vacuo. The residue is dissolved in DCM (50 mL) and the resulting solution is added dropwise to saturated aqueous ammonium hydroxide (200 mL) at RT. The resulting mixture is stirred for 30 min and then filtered. The filter cake is rinsed with H2O (30 mL×2). The filtrate is acidified with conc. HCl to adjust the pH to 4-5. The solid is collected by filtration, rinsed with water and dried in vacuo to afford the product, 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carboxamide (H-2).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue is dissolved in DCM (50 mL)
  3. additionthe resulting solution is added dropwise to saturated aqueous ammonium hydroxide (200 mL) at RT
  4. stirringThe resulting mixture is stirred for 30 min
  5. filtrationfiltered
  6. washThe filter cake is rinsed with H2O (30 mL×2)
  7. filtrationThe solid is collected by filtration
  8. washrinsed with water
  9. customdried in vacuo

Sources & evidence

ORD record
ord-1b2e2ef6154f4ab0b4a2f6f307cb4094
Source dataset
uspto-grants-2014_12
Patent number
US08901133B2

Reaction notes

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