Trimethylsilyldiazomethane → 2-chloro-7-(1-ethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid methyl ester

HRID 2189321Notes

Reaction equation

HRID 2189321 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[CH:10]=[C:9]([C:11]([OH:13])=[O:12])[N:8]([CH:14]([CH2:17][CH3:18])[CH2:15][CH3:16])[C:6]=2[N:7]=1.[CH3:19][Si](C=[N+]=[N-])(C)C>CO>[CH3:19][O:12][C:11]([C:9]1[N:8]([CH:14]([CH2:17][CH3:18])[CH2:15][CH3:16])[C:6]2[N:7]=[C:2]([Cl:1])[N:3]=[CH:4][C:5]=2[CH:10]=1)=[O:13]

Participants

4

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 735546592-Chloro-7-(pentan-3-yl)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid

Product 1

HCID 866373482-chloro-7-(1-ethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-chloro-7-(1-ethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid (13 mg, 0.049 mmol) in MeOH (0.5 mL) is added (trimethylsilyl)diazomethane (0.07 mL of a 2.0 M in hexanes). The reaction mixture is stirred for 2 h and concentrated in vacuo to give 13 mg of 2-chloro-7-(1-ethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid methyl ester. The crude product is used as it is.

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8c8b99be0cfa46afab1e359a296308e4
Source dataset
uspto-grants-2012_12
Patent number
US08324225B2

Reaction notes

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