Formamide → HCID 136336816, compound

HRID 1469106Notes

Reaction equation

HRID 1469106 reaction equation
[NH2:1][C:2]1[C:3]([C:26]([O:28]C)=O)=[N:4][C:5]([C:8]2[CH:9]=[C:10]3[N:16]=[C:15]([CH3:17])[N:14]([CH2:18][O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])[C:11]3=[N:12][CH:13]=2)=[CH:6][CH:7]=1.[CH:30]([NH2:32])=O>>[CH3:17][C:15]1[N:14]([CH2:18][O:19][CH2:20][CH2:21][Si:22]([CH3:24])([CH3:23])[CH3:25])[C:11]2=[N:12][CH:13]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]4[N:1]=[CH:30][NH:32][C:26](=[O:28])[C:3]=4[N:4]=3)[CH:9]=[C:10]2[N:16]=1

Participants

3

Reactant 2

HCID 713FormamideHCID 86692086HCID 86692086, compound

Product 1

HCID 136336816HCID 136336816, compoundYield 36%

Procedure

1.00 g of methyl 3-amino-6-[2-methyl-3-(2-trimethylsilanylethoxymethyl)-3H-imidazo[4,5-b]pyridin-6-yl]pyridine-2-carboxylate in 16 ml of formamide are heated at 130° C. under nitrogen in a flask until the reaction is complete (HPLC check, about 48 hours). The excess formamide is distilled off (120° C., 1 mbar). The residue is dissolved in dichloromethane, washed with water, dried and purified by means of column chromatography (gradient EA: methanol 0-50% in 15 min), giving 0.40 g of 6-[2-methyl-3-(2-trimethylsilanylethoxymethyl)-3H-imidazo[4,5-b]pyridin-6-yl]-3H-pyrido[3,2-d]pyrimidin-4-one as reddish solid (yield 36%, content 95%); MS-FAB (M+H+)=409.1; Rf (polar method): 2.01 min.

Workup

  1. custom(HPLC check, about 48 hours)
  2. distillationThe excess formamide is distilled off (120° C., 1 mbar)
  3. dissolutionThe residue is dissolved in dichloromethane
  4. washwashed with water
  5. customdried
  6. custompurified by means of column chromatography (gradient EA: methanol 0-50% in 15 min)

Sources & evidence

ORD record
ord-d7c66a706ef0446ab3ebb77bf5f4504d
Source dataset
uspto-grants-2015_04
Patent number
US09006255B2

Reaction notes

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