Sodium Hydroxide → tert-butyl (3-(5-methyl-2-(methylsulfonyl)-7-oxopyrido[2,3-d]pyrimidin-8(7H)-yl)phenyl)carbamate

HRID 527401Notes

Reaction equation

HRID 527401 reaction equation
[CH3:1][C:2]1[C:11]2[CH:10]=[N:9][C:8]([S:12][CH3:13])=[N:7][C:6]=2[N:5]([C:14]2[CH:15]=[C:16]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH:17]=[CH:18][CH:19]=2)[C:4](=[O:28])[CH:3]=1.C1C=C(Cl)C=C(C(OO)=[O:37])C=1.[OH-:40].[Na+]>C(Cl)Cl>[CH3:1][C:2]1[C:11]2[CH:10]=[N:9][C:8]([S:12]([CH3:13])(=[O:37])=[O:40])=[N:7][C:6]=2[N:5]([C:14]2[CH:15]=[C:16]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:24])([CH3:26])[CH3:25])[CH:17]=[CH:18][CH:19]=2)[C:4](=[O:28])[CH:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 86732009tert-butyl (3-(5-methyl-2-(methylthio)-7-oxopyrido[2,3-d]pyrimidin-8(7H)-yl)phenyl)carbamate

Product 1

HCID 86732012tert-butyl (3-(5-methyl-2-(methylsulfonyl)-7-oxopyrido[2,3-d]pyrimidin-8(7H)-yl)phenyl)carbamateYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

At RT, tert-butyl (3-(5-methyl-2-(methylthio)-7-oxopyrido[2,3-d]pyrimidin-8(7H)-yl)phenyl)carbamate (54) (440 mg, 1.10 mmol) in DCM (10 mL) was treated with MCPBA (75 wt. %, 681 mg, 2.76 mmol) and stirred for 90 min. The reaction mixture was diluted with DCM (25 mL), treated with ice and 1 N NaOH (30 mL). The DCM layer was separated and the aqueous layer was extracted with an additional amount of DCM (2×20 mL), dried over Na2SO4 and concentrated to furnish tert-butyl (3-(5-methyl-2-(methylsulfonyl)-7-oxopyrido[2,3-d]pyrimidin-8(7H)-yl)phenyl)carbamate (451 mg, 1.05 mmol, 95% yield) as an off-white foam. The crude material was used without purification. m/z (ESI, +ve ion) 453.0 (M+Na)+. 1H NMR (400 MHz, CDCl3) δ ppm 9.11 (1H, s), 7.60 (1H, br. s.), 7.45 (1H, t, J=8.0 Hz), 7.23 (1H, dt, J=8.2, 1.0 Hz), 6.91 (1H, ddd, J=7.9, 1.9, 0.8 Hz), 6.80 (1H, d, J=1.4 Hz), 6.60 (1H, s), 3.04 (3H, s), 2.60 (3H, d, J=1.2 Hz), 1.49 (9H, s).

Workup

  1. customThe DCM layer was separated
  2. extractionthe aqueous layer was extracted with an additional amount of DCM (2×20 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-28c45b3e6b2945e3af5bdcf5f21d4524
Source dataset
uspto-grants-2016_05
Patent number
US09346801B2

Reaction notes

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