Sodium ethoxide → HCID 178451653, compound

HRID 1930587Notes

Reaction equation

HRID 1930587 reaction equation
O=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH:3]1[C:15]([O:17]C)=O.[Br:19][C:20]1[CH:25]=[CH:24][C:23]([NH:26][C:27]([NH2:29])=[NH:28])=[CH:22][CH:21]=1.[O-]CC.[Na+]>C(O)C>[Br:19][C:20]1[CH:21]=[CH:22][C:23]([NH:26][C:27]2[N:28]=[C:15]([OH:17])[C:3]3[CH2:4][N:5]([C:8]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:9])[CH2:6][CH2:7][C:2]=3[N:29]=2)=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 112768931-tert-Butyl 3-methyl 4-oxopiperidine-1,3-dicarboxylateHCID 178512467HCID 178512467, compound

Product 1

HCID 178451653HCID 178451653, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-tert-Butyl 3-methyl 4-oxopiperidine-1,3-dicarboxylate (1 g, 3.89 mmol), 1-(4-bromophenyl)guanidine (0.832 g, 3.89 mmol) and sodium ethoxide (0.264 g, 3.89 mmol) in ethanol (8 mL) were heated to 100° C. in a microwave reactor for 15 minutes. The reaction mixture was allowed to reach room temperature, the solid obtained was filtered and washed with cold ethanol and dried in a vacuum oven yielding tert-butyl 2-(4-bromophenylamino)-4-hydroxy-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate (1.45 g, 72%). The compound was used in the next step without purification. MS (ESI) (M+H) m/z 423

Workup

  1. customto reach room temperature
  2. customthe solid obtained
  3. filtrationwas filtered
  4. washwashed with cold ethanol
  5. customdried in a vacuum oven

Sources & evidence

ORD record
ord-ca103b86dc134f519955f2541cb619ef
Source dataset
uspto-grants-2012_05
Patent number
US08188101B2

Reaction notes

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