Dimethyl Sulfoxide → (R)-8-cyclopentyl-7-ethyl-5-methyl-6-oxo-5,6,7,8-tetrahydropteridine-2-carboxylic acid

HRID 2093705Notes

Reaction equation

Cl[C:2]1[N:11]=[CH:10][C:9]2[N:8]([CH3:12])[C:7](=[O:13])[C@@H:6]([CH2:14][CH3:15])[N:5]([CH:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)[C:4]=2[N:3]=1.C[C:22]([OH:25])(C)C.C1C=CC(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CS(C)=[O:57]>CC([O-])=O.CC([O-])=O.[Pd+2]>[CH:16]1([N:5]2[C:4]3[N:3]=[C:2]([C:22]([OH:25])=[O:57])[N:11]=[CH:10][C:9]=3[N:8]([CH3:12])[C:7](=[O:13])[C@H:6]2[CH2:14][CH3:15])[CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

Conditions

Temperature: 80 °C

Procedure

Intermediate B (10.0 g, 34.01 mmol) was dissolved in 15 mL of DMSO and 185 mL of tBuOH and Pd(OAc)2 (1.14 g, 5.1 mmol), DPPP (2.2 g, 5.1 mmol) and TEA (7.7 g, 76.5 mmol) were added. The solution was stirred at 80° C. for 10 h under CO (10 atm). The solvent was removed under reduced pressure and the residue was dissolved in EtOAc. The organic layer was washed with water and brine, dried with Na2SO4, purified by silica gel column (DCM:MeOH=20:1) to give (R)-8-cyclopentyl-7-ethyl-5-methyl-6-oxo-5,6,7,8-tetrahydropteridine-2-carboxylic acid (compound I-245, 2.2 g) as a yellow solid.

Workup

customThe solvent was removed under reduced pressure
dissolutionthe residue was dissolved in EtOAc
washThe organic layer was washed with water and brine
dry with materialdried with Na2SO4
custompurified by silica gel column (DCM:MeOH=20:1)

Sources & evidence

ORD record: ord-c469347370f446abbadcb6bb0fcc0449
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08445503B2

Reaction notes

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