Formic Acid → 3-(5-(4-chlorobenzyl)-6-(2-isopropylphenyl)-1-methyl-2,4-dioxo-1,2-dihydro pyrido[2,3-d]pyrimidin-3(4H)-yl)propyl formate

HRID 60495Notes

Reaction equation

[Si]([O:8][CH2:9][CH2:10][CH2:11][N:12]1[C:17](=[O:18])[C:16]2[C:19]([CH:32]([C:34]3[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][CH:35]=3)O)=[C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[CH:29]([CH3:31])[CH3:30])[CH:21]=[N:22][C:15]=2[N:14]([CH3:41])[C:13]1=[O:42])(C(C)(C)C)(C)C.[CH:43](O)=[O:44]>[Zn]>[CH:43]([O:8][CH2:9][CH2:10][CH2:11][N:12]1[C:17](=[O:18])[C:16]2[C:19]([CH2:32][C:34]3[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][CH:35]=3)=[C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[CH:29]([CH3:30])[CH3:31])[CH:21]=[N:22][C:15]=2[N:14]([CH3:41])[C:13]1=[O:42])=[O:44]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 3-(3-((tert-butyldimethylsilyl)oxy)propyl)-5-((4-chlorophenyl) (hydroxy)methyl)-6-(2-isopropylphenyl)-1-methylpyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (See Compound 20, step 6, 50 mg, 0.086 mmol) in HCOOH (5 mL) was added Zn dust (56.6 mg, 0.86 mmol). The reaction was heated at 100° C. for 3 h, cooled to RT and filtered. The filtrate was concentrated and dried to give 3-(5-(4-chlorobenzyl)-6-(2-isopropylphenyl)-1-methyl-2,4-dioxo-1,2-dihydropyrido[2,3-d]pyrimidin-3(4H)-yl)propyl formate (20 mg, 48.0% yield) as a brown oil. LCMS: [MH+—OH] 506 and TR=2.062 min. Used without further purification.

Workup

temperaturecooled to RT
filtrationfiltered
concentrationThe filtrate was concentrated
customdried

Sources & evidence

ORD record: ord-31b57e16863d4c21a90f00aa7b150b80
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09440972B2

Reaction notes

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