Tetrahydrofuran → [[2-methoxy-5-(aminooxoacetyl)-6-ethyl-7-(phenylmethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]acetic acid methyl ester

HRID 1934429Notes

Reaction equation

HRID 1934429 reaction equation
[CH3:1][O:2][C:3](=[O:33])[CH2:4][O:5][C:6]1[C:7]2[C:18]([C:19](=[O:23])[C:20]([NH2:22])=[O:21])=[C:17]([CH2:24][CH3:25])[N:16]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:8]=2[N:9]=[C:10](S(C)(=O)=O)[N:11]=1.[O:34]1CCC[CH2:35]1>CO.C[O-].[Na+]>[CH3:1][O:2][C:3](=[O:33])[CH2:4][O:5][C:6]1[C:7]2[C:18]([C:19](=[O:23])[C:20]([NH2:22])=[O:21])=[C:17]([CH2:24][CH3:25])[N:16]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:8]=2[N:9]=[C:10]([O:34][CH3:35])[N:11]=1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 69558105[[2-(methylsulfonyl)-5-(aminooxoacetyl)-6-ethyl-7-(phenylmethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy] acetic acid methyl ester

Product 1

HCID 69557788[[2-methoxy-5-(aminooxoacetyl)-6-ethyl-7-(phenylmethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]acetic acid methyl ester

Reagents, catalysts & solvents 2

HCID 10942334Sodium MethoxideCatalystHCID 887MethanolSolvent2×

Procedure

To a solution of 150 mg (0.316 mmol) of [[2-(methylsulfonyl)-5-(aminooxoacetyl)-6-ethyl-7-(phenylmethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy] acetic acid methyl ester in 3 mL of tetrahydrofuran and 0.5 mL of methanol was added 4 drops of 28% sodium methoxide in methanol solution. The reaction was stirred at ambient temperature for 3 hours. The reaction was quenched by the addition of 3 mL of saturated sodium bicarbonate solution and the phases separated. The organic phase was dried with sodium sulfate and concentrated to a yellow solid. The solid was purified by flash chromatography (5.0 g silica, ethyl acetate) to provide 41 mg of [[2-methoxy-5-(aminooxoacetyl)-6-ethyl-7-(phenylmethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]acetic acid methyl ester as an off white solid. nmr (500 MHz, CDCl3) δ1.11 (t, J=7.5 Hz, 3H), 2.90 (q, J=7.5 Hz, 2H), 3.77 (s, 3H), 3.96 (s, 3H), 5.04 (s, 2H), 5.43 (s, 2H), 5.74 (s, 1H), 6.58 (s, 1H), 7.16 (d, J=7.0 Hz, 2H), 7.29 (m, 3H)

Workup

  1. customThe reaction was quenched by the addition of 3 mL of saturated sodium bicarbonate solution
  2. customthe phases separated
  3. dry with materialThe organic phase was dried with sodium sulfate
  4. concentrationconcentrated to a yellow solid
  5. customThe solid was purified by flash chromatography (5.0 g silica, ethyl acetate)

Sources & evidence

ORD record
ord-367e667a1e394c10a38a80def4e82cef
Source dataset
uspto-grants-2002_05
Patent number
US06384041B1

Reaction notes

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