Formamide → HCID 178422981, compound

HRID 1192406Notes

Reaction equation

HRID 1192406 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].[CH:12]([NH2:14])=O>>[CH3:11][C:9]1[CH:8]=[CH:7][C:3]2[C:4]([OH:5])=[N:14][CH:12]=[N:1][C:2]=2[N:10]=1

Participants

3

Reactant 2

HCID 713FormamideHCID 27344322-AMINO-6-METHYLNICOTINIC ACID

Product 1

HCID 178422981HCID 178422981, compoundYield 51.8%

Conditions

Temperature
170 °C

Procedure

A mixture of 2-Amino-6-methyl-nicotinic acid (1.44 g, 9.46 mmol) and formamide (8.0 g, 178 mmol) was stirred at 170° C. for 2 hours. After cooling, the mixture was quenched with water (4 mL). The precipitate was filtered, washed with water and dried to afford 7-Methyl-pyrido[2,3-d]pyrimidin-4-ol (0.79 g, 51%). 1H NMR (CDCl3, 400 MHz) δ 8.49 (d, J=8.4 Hz, 1H), 8.22 (s, 1H), 7.35 (d, J=8.0 Hz, 1H), 2.75 (s, 3H). MS (APCI+) [M+H]+162.

Workup

  1. temperatureAfter cooling
  2. customthe mixture was quenched with water (4 mL)
  3. filtrationThe precipitate was filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-ff22f0f053b149e48bd5673727901ea3
Source dataset
uspto-grants-2014_03
Patent number
US08680114B2

Reaction notes

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