Sodium hydride → 1-tert-Butyl-3-[7-(3-tert-butylureido)-6-o-tolyl-pyrido[2,3-d]pyrimidin-2-yl]urea

HRID 3409Notes

Reaction equation

HRID 3409 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[CH:11]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[CH3:18])[C:9]([NH2:19])=[N:8][C:6]=2[N:7]=1.[H-].[Na+].[C:22]([N:26]=[C:27]=[O:28])([CH3:25])([CH3:24])[CH3:23]>CN(C)C=O>[C:22]([NH:26][C:27]([NH:1][C:2]1[N:3]=[CH:4][C:5]2[CH:11]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[CH3:18])[C:9]([NH:19][C:27]([NH:26][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:28])=[N:8][C:6]=2[N:7]=1)=[O:28])([CH3:25])([CH3:24])[CH3:23]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 62412tert-Butyl isocyanateHCID 218500312,7-Diamino-6-o-tolyl-pyrido[2,3-d]pyrimidine

Product 1

HCID 154345561-tert-Butyl-3-[7-(3-tert-butylureido)-6-o-tolyl-pyrido[2,3-d]pyrimidin-2-yl]urea

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 0.5 g of 2,7-diamino-6-o-tolyl-pyrido[2,3-d]pyrimidine, prepared as described above in Example 1, in 10 mL of dimethylformamide is reacted with 0.16 g of 60% sodium hydride and stirred at ambient temperature for 1.5 hours. To the suspension is added 0.49 mL of t-butylisocyanate and the mixture stirred overnight at ambient temperature. The reaction mixture is filtered to remove insoluble salts and the filtrate evaporated under reduced pressure. The residue is diluted with water, the insoluble crude product collected by filtration and dried in vacuo. Crystallization from a hexane:ethyl acetate: dichloromethane mixture (3:2:5 v/v/v) afforded the title compound, mp 209°-212° C. dec.

Workup

  1. customprepared
  2. stirringthe mixture stirred overnight at ambient temperature
  3. filtrationThe reaction mixture is filtered
  4. customto remove insoluble salts
  5. customthe filtrate evaporated under reduced pressure
  6. additionThe residue is diluted with water
  7. filtrationthe insoluble crude product collected by filtration
  8. customdried in vacuo
  9. customCrystallization from a hexane

Sources & evidence

ORD record
ord-8859698c10bb4c7b910c576bf44215d1
Source dataset
uspto-grants-1998_03
Patent number
US05733913

Reaction notes

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