Aniline → HCID 22607753, compound

HRID 2307795Notes

Reaction equation

HRID 2307795 reaction equation
Cl[C:2]1[C:3]2[CH:11]=[CH:10][C:9]([Cl:12])=[N:8][C:4]=2[N:5]=[CH:6][N:7]=1.[NH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1COCC1.CC(O)C>[Cl:12][C:9]1[CH:10]=[CH:11][C:3]2[C:2]([NH:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[N:7][CH:6]=[N:5][C:4]=2[N:8]=1

Participants

5

Reactant 2

HCID 6115AnilineHCID 226077594,7-Dichloropyrido[2,3-d]pyrimidine

Product 1

HCID 22607753HCID 22607753, compound

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of Example 140D (0.5 g, 2.5 mmol), and aniline (0.23 mL, 2.5 mmol) in THF (25 mL) and 2-propanol (2.5 mL) was stirred at 0° C. for 1 h then at room temperature for 2 days. The THF was evaporated off and the residue was taken into ethyl acetate (75 ml), washed with water (50 ml) and brine (50 ml). The ethyl acetate was evaporated off and the residue was purified by flash column chromatography on silica gel, eluting with 1:1 ethyl acetate/hexane. Recovered 0.15 g of product (23%). MS (ESI) m/z 390 (M+H)+.

Workup

  1. customThe THF was evaporated off
  2. washwashed with water (50 ml) and brine (50 ml)
  3. customThe ethyl acetate was evaporated off
  4. customthe residue was purified by flash column chromatography on silica gel
  5. washeluting with 1:1 ethyl acetate/hexane
  6. customRecovered 0.15 g of product (23%)

Sources & evidence

ORD record
ord-8e7993698e5047e3ac448c6e4530fcf1
Source dataset
uspto-grants-2004_12
Patent number
US06831175B2

Reaction notes

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