Trimethylsilyldiazomethane → HCID 59924897, compound

HRID 2300786Notes

Reaction equation

HRID 2300786 reaction equation
[C:1]1([C@@H:7]([NH:9][C:10]2[N:15]=[C:14]([N:16]3[C:20]4[CH:21]=[C:22]([C:25]([OH:27])=[O:26])[CH:23]=[CH:24][C:19]=4[N:18]=[CH:17]3)[CH:13]=[CH:12][N:11]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:28][Si](C=[N+]=[N-])(C)C>C1C=CC=CC=1.CO>[C:1]1([C@@H:7]([NH:9][C:10]2[N:15]=[C:14]([N:16]3[C:20]4[CH:21]=[C:22]([C:25]([O:27][CH3:28])=[O:26])[CH:23]=[CH:24][C:19]=4[N:18]=[CH:17]3)[CH:13]=[CH:12][N:11]=2)[CH3:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 69961483HCID 69961483, compound

Product 1

HCID 59924897HCID 59924897, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 887MethanolSolvent

Procedure

To a solution of 2-[(S)-1-phenylethylamino]-4-[6-carboxy-benzimidazol-1-yl]pyrimidine in 0.2 mL of benzene and 0.1 mL of methanol was added 0.015 mL of (trimethylsilyl)diazomethane (2 M in hexanes). The solution was stirred for 30 min at room temperature then concentrated. The product was purified by chromatography to afford the title compound. Partial 1H NMR (500 MHz CD3OD): δ 8.9 (s, 1H); 8.63 (br, 1H); 8.42 (d J=5.0 Hz, 1H); 8.09 (d J=11 Hz, 1H); 7.87 (d J=11 Hz, 1H); 6.83 (d J=5.0 Hz, 1H); 5.29 m, 1H); 3.98 (s, 3H); 1.64 (d J=7.0 Hz, 3H).

Workup

  1. concentrationthen concentrated
  2. customThe product was purified by chromatography

Sources & evidence

ORD record
ord-3231908b46d54335b831b29b8fea8d9a
Source dataset
uspto-grants-2002_12
Patent number
US06498165B1

Reaction notes

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