Methanamine--water (1/1) → 4-(4-Fluorophenyl)-2-(methylamino)pyrimidin-5-ol

HRID 1692243Notes

Reaction equation

HRID 1692243 reaction equation
[NH2:1][C:2]1[O:3][C:4]([C:7]([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)=O)=[CH:5][N:6]=1.O.[CH3:17][NH2:18]>C(O)(C)(C)C>[F:15][C:12]1[CH:13]=[CH:14][C:9]([C:7]2[C:4]([OH:3])=[CH:5][N:6]=[C:2]([NH:18][CH3:17])[N:1]=2)=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 13000549Methanamine--water (1/1)HCID 66905466(2-Amino-1,3-oxazol-5-yl)(4-fluorophenyl)methanone

Product 1

HCID 594366134-(4-Fluorophenyl)-2-(methylamino)pyrimidin-5-olYield 66%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
50 °C

Procedure

(2-Amino-1,3-oxazol-5-yl)(4-fluorophenyl)methanone (US2005032859, 1 g, 4.85 mmol) and 40% methyl amine water in excess (50 mL) were combined in tert-butanol (50 mL). The mixture was stirred at 50° C. under nitrogen for 2 hours. The mixture was concentrated in vacuo. The residue was filtered through a pad of silica gel using neat ethyl acetate as eluant. The solution was concentrated in vacuo to afford 0.73 g (66%) of 4-(4-fluorophenyl)-2-(methylamino)pyrimidin-5-ol as a crystalline brown solid. MS m/z 220 [M]+

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. filtrationThe residue was filtered through a pad of silica gel using neat ethyl acetate as eluant
  3. concentrationThe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-bafc5adccb4f4e0d8a94a70d981148b4
Source dataset
uspto-grants-2012_04
Patent number
US08153814B2

Reaction notes

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