Pyridine → HCID 69558434, compound

HRID 1934424Notes

Reaction equation

HRID 1934424 reaction equation
[CH3:1][O:2][C:3](=[O:24])[CH2:4][O:5][C:6]1[C:7]2[CH:14]=[C:13]([CH2:15][CH3:16])[N:12]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:8]=2[N:9]=[CH:10][N:11]=1.[C:25](Cl)(=[O:29])[C:26](Cl)=[O:27].[N:31]1C=CC=CC=1.[OH-].[NH4+]>C(Cl)(Cl)Cl.O>[CH3:1][O:2][C:3](=[O:24])[CH2:4][O:5][C:6]1[C:7]2[CH:14]=[C:13]([CH2:15][CH3:16])[N:12]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:8]=2[N:9]=[CH:10][N:11]=1.[CH3:1][O:2][C:3](=[O:24])[CH2:4][O:5][C:6]1[C:7]2[C:14]([C:25](=[O:29])[C:26]([NH2:31])=[O:27])=[C:13]([CH2:15][CH3:16])[N:12]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:8]=2[N:9]=[CH:10][N:11]=1

Participants

8

Reactant 4

HCID 1049PyridineHCID 14923Ammonium HydroxideHCID 65578Oxalyl chlorideHCID 69558434HCID 69558434, compound

Product 2

HCID 9843682HCID 9843682, compoundYield 45%HCID 69558434HCID 69558434, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

To a solution of 831 mg (2.55 mmol) of [[6-ethyl-7-(phenylmethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]acetic acid methyl ester in 20 mL of chloroform was added 0.67 mL of oxalyl chloride followed by 0.30 mL of pyridine. The reaction was stirred for 18 hours at ambient temperature then poured into a solution prepared from 2.0 mL of concentrated ammonium hydroxide and 8.0 mL of water. The reaction was partitioned by the addition of 20 mL of methylene chloride and 10 mL of water. The organic phase was dried with sodium sulfate and concentrated. The residue was purified by flash chromatography (100 g of silica, ethyl acetate) to provide 420 mg (51%) of [[6-ethyl-7-(phenylmethyl)-7H-pyrrolo[2, 3-d]pyrimidin-4-yl]oxy]acetic acid methyl ester and 455 mg (45%) of [[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) δ1.13 (t, J=7.5 Hz, 3H), 2.95 (q, J=7.5 Hz, 2H), 3.77 (s, 3H), 5.06 (s, 2H), 5.53 (s, 2H), 6.28 (s, 1H), 6.70 (s, 1H), 7.13 (d, J=6.7 Hz, 2H), 7.27 (m, 3H), 8.46 (s, 1H)

Workup

  1. additionthen poured into a solution
  2. customThe reaction was partitioned by the addition of 20 mL of methylene chloride and 10 mL of water
  3. dry with materialThe organic phase was dried with sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography (100 g of silica, ethyl acetate)

Sources & evidence

ORD record
ord-84b251dd4b234328877c8d4edb9c1161
Source dataset
uspto-grants-2002_05
Patent number
US06384041B1

Reaction notes

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