Pyridine → HCID 9801656, compound

HRID 1934425Notes

Reaction equation

HRID 1934425 reaction equation
[CH3:1][O:2][C:3](=[O:25])[CH2:4][O:5][C:6]1[C:7]2[CH:15]=[C:14]([CH2:16][CH3:17])[N:13]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:8]=2[N:9]=[C:10]([CH3:12])[N:11]=1.[C:26](Cl)(=[O:30])[C:27](Cl)=[O:28].[N:32]1C=CC=CC=1.[OH-].[NH4+]>C(Cl)(Cl)Cl.O>[CH3:1][O:2][C:3](=[O:25])[CH2:4][O:5][C:6]1[C:7]2[C:15]([C:26](=[O:30])[C:27]([NH2:32])=[O:28])=[C:14]([CH2:16][CH3:17])[N:13]([CH2:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:8]=2[N:9]=[C:10]([CH3:12])[N:11]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 14923Ammonium HydroxideHCID 65578Oxalyl chlorideHCID 69559023HCID 69559023, compound

Product 1

HCID 9801656HCID 9801656, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

To a solution of 715 mg (2.10 mmol) of [[2-methyl-6-ethyl-7-(phenylmethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]acetic acid methyl ester in 15 mL of chloroform was added 0.55 mL of oxalyl chloride followed by 0.25 mL of pyridine. The reaction was stirred for 18 hours at ambient temperature then poured into a solution prepared from 1.7 mL of concentrated ammonium hydroxide and 5.8 mL of water. The reaction was partitioned by the addition of 15 mL of methylene chloride and a small amount of solid residue was removed by filtration. The organic phase was dried with sodium sulfate and concentrated to an off-white solid. The solid was purified by flash chromatography (100 g of silica, ethyl acetate) to provide 740 mg (86%) of [[2-methyl-5-(aminooxoacetyl)-6-ethyl-7-(phenylmethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]acetic acid methyl ester as a white solid. nmr (500 MHz, CDCl3) δ1.10 (t, J=7.5 Hz, 3H), 2.59 (s, 3H), 2.91 (q, J=7.5 Hz, 2H), 3.76 (s, 3H), 5.04 (s, 2H), 5.50 (s, 2H), 6.25 (s, 1H), 6.66 (s, 1H), 7.13 (d, J=6.9 Hz, 2H), 7.28 (m, 3H)

Workup

  1. additionthen poured into a solution
  2. customThe reaction was partitioned by the addition of 15 mL of methylene chloride
  3. customa small amount of solid residue was removed by filtration
  4. dry with materialThe organic phase was dried with sodium sulfate
  5. concentrationconcentrated to an off-white solid
  6. customThe solid was purified by flash chromatography (100 g of silica, ethyl acetate)

Sources & evidence

ORD record
ord-94c87a81de0541f680ac66a1a0708a0b
Source dataset
uspto-grants-2002_05
Patent number
US06384041B1

Reaction notes

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