Azetidine hydrochloride → 2-(Azetidin-1-ylcarbonyl)-5-bromopyrimidine

HRID 1177151Notes

Reaction equation

HRID 1177151 reaction equation
CN(C)C(C1C=[CH:9][C:8](Br)=[CH:7][N:6]=1)=O.[Br:13][C:14]1[CH:15]=[N:16][C:17]([C:20]([OH:22])=O)=[N:18][CH:19]=1.Cl.N1CCC1>>[N:6]1([C:20]([C:17]2[N:18]=[CH:19][C:14]([Br:13])=[CH:15][N:16]=2)=[O:22])[CH2:7][CH2:8][CH2:9]1

Participants

4

Reactant 3

HCID 12308726Azetidine hydrochlorideHCID 164629705-Bromopyrimidine-2-carboxylic acidHCID 228316185-bromo-N,N-dimethylpicolinamide

Product 1

HCID 536296392-(Azetidin-1-ylcarbonyl)-5-bromopyrimidine

Procedure

The title compound was prepared in a similar manner as described for Intermediate 161a, from 5-bromopyrimidine-2-carboxylic acid (1.60 g, 7.877 mmol) and azetidine hydrochloride (1.11 g, 11.8 mmol) to give a yellow solid (331 mg, 17% yield). 1H NMR (400 MHz, CDCl3) δ 8.92 (s, 2 H) 4.64 (t, J=7.71 Hz, 2 H) 4.29 (t, J=7.83 Hz, 2 H) 2.29-2.41 (m, 2 H); LCMS for C8H8BrN3O m/z 241.00 and 243.00 (M+H)+.

Sources & evidence

ORD record
ord-8613d21f8bde44db874915c9334883e4
Source dataset
uspto-grants-2010_11
Patent number
US07842713B2

Reaction notes

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