Sodium Carbonate → tert-butyl (3-(6-ethyl-2-(methylsulfinyl)-7-oxopyrido[2,3-d]pyrimidin-8(7H)-yl)phenyl)carbamate

HRID 527413Notes

Reaction equation

[CH2:1]([C:3]1[C:14](=[O:15])[N:13]([C:16]2[CH:17]=[C:18]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH:19]=[CH:20][CH:21]=2)[C:6]2[N:7]=[C:8]([S:11][CH3:12])[N:9]=[CH:10][C:5]=2[CH:4]=1)[CH3:2].ClC1C=C(C=CC=1)C(OO)=[O:35].C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[CH2:1]([C:3]1[C:14](=[O:15])[N:13]([C:16]2[CH:17]=[C:18]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH:19]=[CH:20][CH:21]=2)[C:6]2[N:7]=[C:8]([S:11]([CH3:12])=[O:35])[N:9]=[CH:10][C:5]=2[CH:4]=1)[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

At 0° C., a suspension of tert-butyl (3-(6-ethyl-2-(methylthio)-7-oxopyrido[2,3-d]pyrimidin-8(7H)-yl)phenyl)carbamate (55) (720 mg, 1.75 mmol) in DCM (15 mL) was treated with 3-chloroperoxybenzoic acid (70 wt. %, 460 mg, 1.87 mmol) in one portion and stirred at 0° C. for 1 h. The reaction mixture was diluted with DCM (15 mL), and treated with ice and a 10% solution of Na2CO3 (ca. 10 mL). The DCM layer was separated and the aqueous layer was extracted with an additional amount of DCM (2×50 mL), dried over sodium sulfate and concentrated to give tert-butyl (3-(6-ethyl-2-(methylsulfinyl)-7-oxopyrido[2,3-d]pyrimidin-8(7H)-yl)phenyl)carbamate (6a) (682 mg, 1.59 mmol, 91% yield) as a light yellow amorphous solid. m/z (ESI, +ve ion) 451.0 (M+Na)+. The crude material was used in the subsequent step without further purification.

Workup

additiontreated with ice
customThe DCM layer was separated
extractionthe aqueous layer was extracted with an additional amount of DCM (2×50 mL)
dry with materialdried over sodium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-f0bacf24056c4ac28762ba30a734c8fe
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346801B2

Reaction notes

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