Diisobutylaluminumhydride → 6-bromo-3-(3-hydroxypropyl)-1-methylpyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione

HRID 60442Notes

Reaction equation

HRID 60442 reaction equation
[Br:1][C:2]1[CH:20]=[N:19][C:5]2[N:6]([CH3:18])[C:7](=[O:17])[N:8]([CH2:11][CH2:12][C:13](OC)=[O:14])[C:9](=[O:10])[C:4]=2[CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C>C1COCC1>[Br:1][C:2]1[CH:20]=[N:19][C:5]2[N:6]([CH3:18])[C:7](=[O:17])[N:8]([CH2:11][CH2:12][CH2:13][OH:14])[C:9](=[O:10])[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 118875436methyl 3-(6-bromo-1-methyl-2,4-dioxo-1,2-dihydropyrido[2,3-d]pyrimidin-3(4H)-yl)propanoate

Product 1

HCID 1188759026-bromo-3-(3-hydroxypropyl)-1-methylpyrido[2,3-d]pyrimidine-2,4(1H,3H)-dioneYield 131.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-60 °C

Procedure

To a solution of methyl 3-(6-bromo-1-methyl-2,4-dioxo-1,2-dihydropyrido[2,3-d]pyrimidin-3(4H)-yl)propanoate (5.1 g, 14.96 mmol) in THF (500 mL) at −60° C., was added diisobutylaluminium hydride (1.5 M in toluene, 40 mL, 60 mmol) dropwise. The reaction was stirred at −60° C. for 3 h, warmed to 0° C., quenched with aq. NH4Cl (150 mL) then extracted with EA (200 mL). The organic layer was washed with brine (100 mL), dried over Na2SO4 and concentrated to give 6-bromo-3-(3-hydroxypropyl)-1-methylpyrido[2,3-d]pyrimidine-2,4 (1H,3H)-dione (6.2 g, >100% yield) as a yellow oil. LCMS: MH+ 314 and TR=0.882 min. Used without further purification.

Workup

  1. temperaturewarmed to 0° C.
  2. customquenched with aq. NH4Cl (150 mL)
  3. extractionthen extracted with EA (200 mL)
  4. washThe organic layer was washed with brine (100 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-01105800bff849d3883a7a1f51b620c0
Source dataset
uspto-grants-2016_09
Patent number
US09440972B2

Reaction notes

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