Dimethylformamide → 4-Chloro-7H-pyrrolo(2,3-d)pyrimidine-5-carboxamide
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]=1Participants
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
- concentrationconcentrated in vacuo
- dissolutionThe residue is dissolved in DCM (50 mL)
- additionthe resulting solution is added dropwise to saturated aqueous ammonium hydroxide (200 mL) at RT
- stirringThe resulting mixture is stirred for 30 min
- filtrationfiltered
- washThe filter cake is rinsed with H2O (30 mL×2)
- filtrationThe solid is collected by filtration
- washrinsed with water
- customdried in vacuo
Sources & evidence
- ORD record
- ord-43636f33b00a4659a16271a806fa3768
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09388183B2
Reaction notes
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