Sodium ethoxide → tert-butyl 2-[4-(1,3-oxazol-5-yl)anilino]-4-oxo-1,5,6,8-tetrahydropyrido[3,4-d]pyrimidine-7-carboxylate

HRID 1930542Notes

Reaction equation

HRID 1930542 reaction equation
[O-]CC.[Na+].O=[C:6]1[CH:11]([C:12]([O:14]CC)=O)[CH2:10][CH2:9][N:8]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:7]1.[O:24]1[C:28]([C:29]2[CH:34]=[CH:33][C:32]([NH:35][C:36]([NH2:38])=[NH:37])=[CH:31][CH:30]=2)=[CH:27][N:26]=[CH:25]1>C(O)C>[OH:14][C:12]1[C:11]2[CH2:10][CH2:9][N:8]([C:17]([O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:18])[CH2:7][C:6]=2[N:38]=[C:36]([NH:35][C:32]2[CH:33]=[CH:34][C:29]([C:28]3[O:24][CH:25]=[N:26][CH:27]=3)=[CH:30][CH:31]=2)[N:37]=1

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 158529891-tert-Butyl 4-ethyl 3-oxopiperidine-1,4-dicarboxylateHCID 1785124711-(4-(Oxazol-5-yl)phenyl)guanidine

Product 1

HCID 178451643tert-butyl 2-[4-(1,3-oxazol-5-yl)anilino]-4-oxo-1,5,6,8-tetrahydropyrido[3,4-d]pyrimidine-7-carboxylateYield 41.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
100 °C

Procedure

Sodium ethoxide (0.476 g, 7.00 mmol) was added to 1-tert-butyl 4-ethyl 3-oxopiperidine-1,4-dicarboxylate (1.899 g, 7.00 mmol, Example 1d) and 1-(4-(oxazol-5-yl)phenyl)guanidine (1.415 g, 7.00 mmol, Example 1e) in ethanol (10 mL). The reaction vial was heated a microwave reactor at 100° C. for 15 minutes. The suspension was diluted with ethanol (5 ml) and the precipitated crude product was filtered off and washed with cold ethanol to give tert-butyl 4-hydroxy-2-(4-(oxazol-5-yl)phenylamino)-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)-carboxylate (1.200 g, 41.9%). No further purification. MS (ESI+)/(ESI−) m/z 410/408

Workup

  1. customthe precipitated crude product
  2. filtrationwas filtered off
  3. washwashed with cold ethanol

Sources & evidence

ORD record
ord-3a822a96d9764fb09167f92ba2460513
Source dataset
uspto-grants-2012_05
Patent number
US08188101B2

Reaction notes

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