Methanol → 2-[Bis(tert-butoxycarbonyl)amino)-5-(2'-methylsulfonylphenyl)pyrimidine

HRID 2186220Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C:9]1[N:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2SC)=[CH:11][N:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O[O:31][S:32]([O-:34])=O.[K+].[CH3:36]O>O>[C:1]([O:5][C:6]([N:8]([C:23]([O:25][C:26]([CH3:27])([CH3:29])[CH3:28])=[O:24])[C:9]1[N:10]=[CH:11][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[S:32]([CH3:36])(=[O:34])=[O:31])=[CH:13][N:14]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

2-[Bis(tert-butoxycarbonyl)amino]-5-(2′-methylthiophenyl)pyrimidine (2.13 g, 5.1 mmol) was dissolved in MeOH (20 mL) and cooled to 0° C. In a separate beaker, a solution of Oxone (5.49 g) was generated by dilution to 27 mL with water. A portion of this solution (17 mL, 5.6 mmol) was removed and adjusted to pH 4.2 with sat. Na3PO4 solution (4.7 mL). This mixture was added to the reaction and stirred 23 hours at room temp. The resulting mixture was diluted with water and extracted with CHCl3. The organics were combined, washed with water and brine, dried over Na2SO4, filtered, and evaporated. The crude product was chromatographed on silica gel (50-100% EtOAc/hexanes) to yield the sulfone (1.28 g, 56%). 1H NMR (CDCl3): δ8.81 (s, 2H), 8.28 (dd, 1H, J=7.6, J′=1.4), 7.72 (m, 2H), 7.39 (dd, 1H, J=7.3, J′=1.4), 2.76 (s, 3H), 1.50 (s, 18H).

Workup

additionThis mixture was added to the reaction
extractionextracted with CHCl3
washwashed with water and brine
dry with materialdried over Na2SO4
filtrationfiltered
customevaporated
customThe crude product was chromatographed on silica gel (50-100% EtOAc/hexanes)

Sources & evidence

ORD record: ord-3c43d7f6bcb8442197a849ed75c8734e
Source dataset: uspto-grants-2002_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06403620B1

Reaction notes

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