Formic Acid → HCID 178422245, compound

HRID 1892130Notes

Reaction equation

HRID 1892130 reaction equation
[NH2:1][C:2]1[NH:3][C:4]([CH3:12])=[CH:5][C:6]=1[C:7](OCC)=[O:8].C(O)=O.[CH3:16][N:17](C=O)C>C(N)=O>[CH3:12][C:4]1[NH:3][C:2]2[N:1]=[CH:16][N:17]=[C:7]([OH:8])[C:6]=2[CH:5]=1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 6228DimethylformamideHCID 14144333Ethyl 2-amino-5-methyl-1H-pyrrole-3-carboxylate

Product 1

HCID 178422245HCID 178422245, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 713FormamideSolvent

Procedure

In a sealed tube, ethyl 2-amino-5-methyl-1H-pyrrole-3-carboxylate (150 mg, 0.9 mmol, prepared according to literature procedures, J. Heterocyclic Chem., 23:1555 (1985)) was dissolved in formamide (4.5 ml), formic acid (2.3 ml) and DMF (1.0 ml) and heated to 155° C. for 12 h. The reaction was concentrated, taken up with NaHCO3 solution, and extracted with DCM to afford 6-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-ol (70 mg, 0.46 mmol, 51%, MS (ES+) [M+H]+=150). This material was dissolved in phosphorous oxychloride (5 ml) and heated to 110° C. for 1 h. The reaction was concentrated, taken up with NaHCO3, and extracted with DCM to give 4-chloro-6-methyl-7H-pyrrolo[2,3-d]pyrimidine (40 mg, 0.23 mmol, 50%). MS (ES+) [M+H]+=168.

Workup

  1. concentrationThe reaction was concentrated
  2. extractionextracted with DCM

Sources & evidence

ORD record
ord-7d996c6f52234fb4b7d205285af97f8d
Source dataset
uspto-grants-2013_08
Patent number
US08507672B2

Reaction notes

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