Trifluoroacetic acid → 1,1-Dimethylethyl 3-[(4,6-dimethyl-2-pyrimidinyl)oxy]-1-azetidinecarboxylate

HRID 2059671Notes

Reaction equation

HRID 2059671 reaction equation
Cl[C:2]1[N:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[N:3]=1.FC(F)(F)C(O)=O.[OH:17][CH:18]1[CH2:21][N:20]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:19]1>>[CH3:9][C:4]1[CH:5]=[C:6]([CH3:8])[N:7]=[C:2]([O:17][CH:18]2[CH2:19][N:20]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:21]2)[N:3]=1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 205502-Chloro-4,6-dimethylpyrimidineHCID 2756801Tert-butyl 3-hydroxyazetidine-1-carboxylate

Product 1

HCID 594183141,1-Dimethylethyl 3-[(4,6-dimethyl-2-pyrimidinyl)oxy]-1-azetidinecarboxylate

Procedure

Compound P24 was prepared according to the general procedure described in the preparation of P21, except that 2-chloro-4,6-dimethylpyrimidine was used in place of 2-bromopyridine, to afford P24. LCMS (ESI) m/z 280.3 (M+1). 1H NMR (400 MHz, CDCl3) δ 1.39 (s, 9H), 2.34 (s, 6H), 3.96 (m, 2H), 4.25 (m, 2H), 5.26 (m, 1H), 6.66 (s, 1H). Compound P24 was deprotected with trifluoroacetic acid as described for tert-butyl 3-hydroxyazetidine-1-carboxylate in the preparation of C19, Example 3 before being used in the coupling step.

Workup

  1. customCompound P24 was prepared
  2. customto afford P24

Sources & evidence

ORD record
ord-791b0ffc7cbf4322943558e8ead2af53
Source dataset
uspto-grants-2012_10
Patent number
US08278295B2

Reaction notes

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