tert-Butanol → Methyl 4-(4-fluorophenyl)-6-(1-methylethyl)-2-(methyl(methylsulfonyl)amino)-5-pyrimidinecarboxylate

HRID 50110

Reaction equation

HRID 50110 reaction equation
[NH2:1][C:2]([CH:17]([CH3:19])[CH3:18])=[C:3]([C:8]([C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=1)=O)[C:4]([O:6][CH3:7])=[O:5].CNS(C)(=O)=O.C(O)(C)(C)C.[C:31]([N:33]([CH3:38])[S:34]([CH3:37])(=[O:36])=[O:35])#[N:32].CC(C)([O-])C.[Na+]>>[F:16][C:13]1[CH:14]=[CH:15][C:10]([C:8]2[C:3]([C:4]([O:6][CH3:7])=[O:5])=[C:2]([CH:17]([CH3:19])[CH3:18])[N:1]=[C:31]([N:33]([S:34]([CH3:37])(=[O:36])=[O:35])[CH3:38])[N:32]=2)=[CH:11][CH:12]=1

Participants

6

Reactant 5

HCID 6386tert-ButanolHCID 97632N-MethylmethanesulfonamideHCID 10219456N-cyano-N-methylmethanesulphonamideHCID 23676156Sodium t-butoxideHCID 178500884HCID 178500884, compound

Product 1

HCID 9929821Methyl 4-(4-fluorophenyl)-6-(1-methylethyl)-2-(methyl(methylsulfonyl)amino)-5-pyrimidinecarboxylateYield 44.8%

Procedure

2.50 g (9.42 mmol) of methyl 3-amino-2-[1-(4-fluorophenyl)methanoyl]-4-methylpent-2-enoate were introduced into 2.08 g (28.3 mmol) of N-methylmethanesulphonamide and 3.49 g (47.1 mmol) of tert-butanol together with 3.79 g (28.3 mmol) of N-cyano-N-methylmethanesulphonamide. 1.87 g (18.8 mmol) of sodium tert-butoxide were added to this suspension at room temperature after the course of 15 min (exothermic). After 4 h at 76° C., the reaction suspension was poured onto 20 g of ice water. The suspension was stirred in an ice bath, and the precipitate was filtered off and washed with water (2×2.5 ml). After drying in a high vacuum, 1.61 g of methyl 4-(4-fluorophenyl)-6-isopropyl-2-(N-methanesulphonyl-N-methylamino)pyrimidine-5-carboxylate were obtained in the form of a pale beige solid.

Workup

  1. filtrationthe precipitate was filtered off
  2. washwashed with water (2×2.5 ml)
  3. customAfter drying in a high vacuum

Sources & evidence

ORD record
ord-fb42980e9c094f758d8d09754f3e9526
Source dataset
uspto-grants-2004_03
Patent number
US06710178B2

Linked notes

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