Tetrahydrofuran → 7-(4-Formylphenyl)-6-phenylpyrido[2,3-d]pyrimidine-2-carboxamide

HRID 2354133Notes

Reaction equation

HRID 2354133 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:11][C:12]3[CH:17]=[N:16][C:15]([C:18]#[N:19])=[N:14][C:13]=3[N:20]=2)=[CH:5][CH:4]=1)=[O:2].C1C[O:30]CC1.C([O-])([O-])=O.[K+].[K+].C(N)(N)=O.OO>O>[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]2[C:10]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:11][C:12]3[CH:17]=[N:16][C:15]([C:18]([NH2:19])=[O:30])=[N:14][C:13]=3[N:20]=2)=[CH:7][CH:8]=1)=[O:2]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 31294Carbamide PeroxideHCID 86078325HCID 86078325, compound

Product 1

HCID 577139577-(4-Formylphenyl)-6-phenylpyrido[2,3-d]pyrimidine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 7-(4-formylphenyl)-6-phenylpyrido[2,3-d]pyrimidine-2-carbonitrile (2-5) (0.100 g, 0.297 mmol) in 2:1 THF:H2O (6 mL) was added K2CO3 (16 mg) and urea peroxide (0.112 g, 1.19 mmol). The mixture was stirred for 1 hr at rt when it was concentrated, diluted with 1:1 H2—O:saturated aqueous Na2CO3, and extracted 3× with CH2Cl2. The combined organics were dried (anhd. Na2SO4), filtered, and concentrated. The crude material was used directly in the next step. LRMS, calc'd: 355.0, found: 355.0

Workup

  1. concentrationwas concentrated
  2. additiondiluted with 1:1 H2—O
  3. extractionsaturated aqueous Na2CO3, and extracted 3× with CH2Cl2
  4. dry with materialThe combined organics were dried (anhd. Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5756562a0f664a6994d8d587ceb1578f
Source dataset
uspto-grants-2010_07
Patent number
US07750151B2

Reaction notes

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