4-Amino-2-(ethylthio)-5-(hydroxymethyl)pyrimidine → 4-Pyrimidinamine, 2-(ethylthio)-

HRID 2354141Notes

Reaction equation

HRID 2354141 reaction equation
[NH2:1][C:2]1[C:7](CO)=[CH:6][N:5]=[C:4]([S:10][CH2:11][CH3:12])[N:3]=1>C(Cl)(Cl)Cl.O=[Mn]=O>[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([S:10][CH2:11][CH3:12])[N:3]=1

Participants

4

Reactant 1

HCID 2254334-Amino-2-(ethylthio)-5-(hydroxymethyl)pyrimidine

Product 1

HCID 5657304-Pyrimidinamine, 2-(ethylthio)-

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6212ChloroformSolvent

Procedure

To a solution of 4-amino-5-hydroxymethyl-2-(ethylthio)pyrimidine (5-1a) (9.6 g, 51.89 mmol) in CHCl3 (1 L) was added MnO2 (86.9 g, 415 mmol, 8 equiv). The suspension was stirred at rt overnight. The mixture was filtered through celite and washed with CHCl3. The combined filtrate was concentrated to give the titled compound (5-2a). 1H-NMR (500 MHz, CDCl3) δ 9.78 (s, 1H), 8.42 (s, 1H), 8.20 (broad, 1H), 5.74 (broad, 1H), 2.55 (q, 2H), 1.38 (t, 3H). LRMS m/z (M+H) Calcd. 184.24, found 184.16.

Workup

  1. filtrationThe mixture was filtered through celite
  2. washwashed with CHCl3
  3. concentrationThe combined filtrate was concentrated

Sources & evidence

ORD record
ord-1973106fc9044484a5cab37b74b97786
Source dataset
uspto-grants-2010_07
Patent number
US07750151B2

Reaction notes

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