Hydrogen Peroxide → 6-hydroxy-1-methyl-3-(3-((tetrahydro-2H-pyran-2-yl)oxy)propyl)pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione

HRID 60487Notes

Reaction equation

HRID 60487 reaction equation
[CH3:1][N:2]1[C:7]2[N:8]=[CH:9][C:10](B3OC(C)(C)C(C)(C)O3)=[CH:11][C:6]=2[C:5](=[O:21])[N:4]([CH2:22][CH2:23][CH2:24][O:25][CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][O:27]2)[C:3]1=[O:32].[OH:33]O>CO>[OH:33][C:10]1[CH:9]=[N:8][C:7]2[N:2]([CH3:1])[C:3](=[O:32])[N:4]([CH2:22][CH2:23][CH2:24][O:25][CH:26]3[CH2:31][CH2:30][CH2:29][CH2:28][O:27]3)[C:5](=[O:21])[C:6]=2[CH:11]=1

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 1317370921-methyl-3-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione

Product 1

HCID 1188754886-hydroxy-1-methyl-3-(3-((tetrahydro-2H-pyran-2-yl)oxy)propyl)pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dioneYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-methyl-3-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (2.8 g, 6.3 mmol) in MeOH (100 mL) at 0° C. was added H2O2 (30% in water, 1.4 mL, 10.6 mmol) dropwise over 5 min. The reaction was allowed to warm slowly to RT, stirred for 16 h, quenched with aq. 1M Na2SO3 solution (100 mL), stirred for 15 min then extracted with EA (3×75 mL). The combined organic layers were dried over Na2SO4 and concentrated to give a residue of 6-hydroxy-1-methyl-3-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (2.1 g, 100% yield) as a solid. LCMS: [MH+-THP] 252 and TR=1.740 min. Used without further purification.

Workup

  1. customquenched with aq. 1M Na2SO3 solution (100 mL)
  2. stirringstirred for 15 min
  3. extractionthen extracted with EA (3×75 mL)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-277f8c89f15347c68540909b5af7773f
Source dataset
uspto-grants-2016_09
Patent number
US09440972B2

Reaction notes

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