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

HRID 610128Notes

Reaction equation

HRID 610128 reaction equation
C(OC([N:8](C(OC(C)(C)C)=O)[C:9]1[N:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[S:21]([CH3:24])(=[O:23])=[O:22])=[CH:11][N:10]=1)=O)(C)(C)C.[ClH:32].O1CCOCC1>>[ClH:32].[NH2:8][C:9]1[N:10]=[CH:11][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[S:21]([CH3:24])(=[O:23])=[O:22])=[CH:13][N:14]=1

Participants

3

Reactant 2

HCID 181772932-[Bis(tert-butoxycarbonyl)amino)-5-(2'-methylsulfonylphenyl)pyrimidineHCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 181772542-Amino-5-(2'-methylsulfonylphenyl)pyrimidine hydrochlorideYield 95%

Procedure

2-[Bis(tert-butoxycarbonyl)amino]-5-(2'-methylsulfonylphenyl) pyrimidine (1.28 g, 2.8 mmol) was suspended in HCl/dioxane (10 mL, 4.0 M) and stirred 20 hours at room temp. The resulting mixture was triturated with Et2O and filtered to yield a white solid (772 mg, 95%). 1H NMR (CDCl3 + few drops MeOD): δ8.53 (s, 2H), 8.22 (dd, 1H, J=7.7, J'=1.8), 7.77 (m, 2H), 7.40 (dd, 1H, J=7.4, J'=1.5), 2.94 (s, 3H).

Workup

  1. customThe resulting mixture was triturated with Et2O
  2. filtrationfiltered

Sources & evidence

ORD record
ord-13df95045f9c421bb72706a51dfee70d
Source dataset
uspto-grants-1999_12
Patent number
US05998424

Reaction notes

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