Sodium Bicarbonate → HCID 57898989, compound

HRID 911067Notes

Reaction equation

HRID 911067 reaction equation
[Br:1][C:2]1[C:3]([S:22][C:23]2[C:24]3[CH2:32][N:31](C(OC(C)(C)C)=O)[CH2:30][CH2:29][C:25]=3[N:26]=[CH:27][N:28]=2)=[CH:4][C:5]([NH:8][C:9]2[S:10][CH:11]=[C:12]([CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:13]=2)=[N:6][CH:7]=1.C([O-])(O)=O.[Na+]>C(O)(C(F)(F)F)=O>[Br:1][C:2]1[C:3]([S:22][C:23]2[C:24]3[CH2:32][NH:31][CH2:30][CH2:29][C:25]=3[N:26]=[CH:27][N:28]=2)=[CH:4][C:5]([NH:8][C:9]2[S:10][CH:11]=[C:12]([CH2:14][CH2:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:13]=2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 86634781tert-Butyl 4-(5-bromo-2-(4-phenethylthiazol-2-ylamino)pyridin-4-ylthio)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate

Product 1

HCID 57898989HCID 57898989, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

tert-Butyl 4-(5-bromo-2-(4-phenethylthiazol-2-ylamino)pyridin-4-ylthio)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate (0.023 g, 0.037 mmol) was dissolved in TFA (2 mL) and stirred at ambient temperature for 2 hours. The solution was neutralized with saturated NaHCO3 and extracted with EtOAc. The organic layer was washed with brine, dried, and concentrated to afford the desired product (0.010 g, 52% yield) as a white solid. 1H NMR (CDCl3) δ 8.66 (s, 1H), 8.51 (s, 1H), 7.14-7.27 (m, 6H), 6.38 (s, 1H), 3.99 (s, 2H), 3.22 (t, 2H), 2.89-2.96 (m, 6H).

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with brine
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c12ab0dd71b9412c94cc7b85e15a9e6a
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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