Sodium hydride → 6-Pyridin-4-yl-pyrido[2,3-d]pyrimidine-2,7-diamine

HRID 3480Notes

Reaction equation

HRID 3480 reaction equation
[H-].[Na+].Cl.[N:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]#[N:12])=[CH:6][CH:5]=1.N1C=CC(CC#N)=CC=1.C(OCC[O-])C.[Na+].[NH2:29][C:30]1[N:35]=[C:34]([NH2:36])[C:33]([CH:37]=O)=[CH:32][N:31]=1>C(OCCO)C>[N:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:11]([NH2:12])=[N:36][C:34]3[N:35]=[C:30]([NH2:29])[N:31]=[CH:32][C:33]=3[CH:37]=2)=[CH:6][CH:5]=1

Participants

7

Reactant 5

HCID 24758Sodium hydrideHCID 3091762,4-Diaminopyrimidine-5-carbaldehydeHCID 41120852-(Pyridin-4-yl)acetonitrileHCID 123966084-Pyridylacetonitrile hydrochlorideHCID 23667900Sodium 2-ethoxyethoxide

Product 1

HCID 218500496-Pyridin-4-yl-pyrido[2,3-d]pyrimidine-2,7-diamine

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent2×

Procedure

To cooled (0° C.) 2-ethoxyethanol (13 mL) was added portionwise 0.30 g of sodium hydride (60% in mineral oil), and the suspension was stirred for 10 minutes. To this suspension was added 1.06 g of 4-pyridylaceto-nitrile hydrochloride, and the mixture was stirred at room temperature for 30 minutes. The neutralized solution of 4-pyridylacetonitrile in 2-ethoxyethanol was added to a reaction mixture containing sodium 2-ethoxyethoxide (prepared from 0.11 g of sodium hydride and 4.76 mL of 2-ethoxyethanol) and 0.9 g of 2,4-diamino-5-pyrimidinecarboxaldehyde. The resulting mixture was heated at reflux for 2 hours, cooled, and the insoluble product washed with diethylether and ethyl acetate to afford the title compound; mp >340° C.; MS(CI).

Workup

  1. stirringthe mixture was stirred at room temperature for 30 minutes
  2. temperatureThe resulting mixture was heated
  3. temperatureat reflux for 2 hours
  4. temperaturecooled
  5. washthe insoluble product washed with diethylether and ethyl acetate

Sources & evidence

ORD record
ord-bdd2ed9a9fea4fb5aa31a3576cfe1141
Source dataset
uspto-grants-1998_03
Patent number
US05733913

Reaction notes

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