Formamide → HCID 136278284, compound

HRID 1469096Notes

Reaction equation

HRID 1469096 reaction equation
[NH2:1][C:2]1[C:3]([C:27]([O:29]C)=O)=[N:4][C:5]([C:8]2[CH:9]=[C:10]3[CH:16]=[CH:15][N:14]([Si](C(C)C)(C(C)C)C(C)C)[C:11]3=[N:12][CH:13]=2)=[CH:6][CH:7]=1.O.[CH:32]([NH2:34])=O>>[NH:14]1[C:11]2=[N:12][CH:13]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]4[N:1]=[CH:32][NH:34][C:27](=[O:29])[C:3]=4[N:4]=3)[CH:9]=[C:10]2[CH:16]=[CH:15]1

Participants

4

Reactant 3

HCID 713FormamideHCID 962WaterHCID 86692085HCID 86692085, compound

Product 1

HCID 136278284HCID 136278284, compoundYield 83%

Procedure

3.80 g of methyl 3-amino-6-(1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-pyridine-2-carboxylate in 60 ml of formamide are heated at 120° C. under nitrogen in a flask until the reaction is complete (HPLC check, about 52 hours). The cooled reaction solution is added to about 50 ml of water, during which a precipitate precipitates out. This is filtered off with suction and dried, giving 2.00 g of 6-(1H-pyrrolo[2,3-b]pyridin-5-yl)-3H-pyrido[3,2-d]pyrimidin-4-one as orange solid (yield 83%, content 98%); MS-FAB (M+H+)=264.1; Rf (polar method): 1.28 min.

Workup

  1. custom(HPLC check, about 52 hours)
  2. customThe cooled reaction solution
  3. customprecipitates out
  4. filtrationThis is filtered off with suction
  5. customdried

Sources & evidence

ORD record
ord-14a5fc929f4a4ab98284e5993185804a
Source dataset
uspto-grants-2015_04
Patent number
US09006255B2

Reaction notes

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