3,3-Difluoroazetidine hydrochloride → HCID 58075837, compound

HRID 2370144Notes

Reaction equation

HRID 2370144 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[CH2:11][O:10][CH2:9][CH:8]([C:12]3[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=3)[C:6]=2[N:7]=1.Cl.[F:21][C:22]1([F:26])[CH2:25][NH:24][CH2:23]1>>[Cl:1][C:2]1[N:3]=[C:4]([N:24]2[CH2:25][C:22]([F:26])([F:21])[CH2:23]2)[C:5]2[CH2:11][O:10][CH2:9][CH:8]([C:12]3[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=3)[C:6]=2[N:7]=1

Participants

3

Reactant 2

HCID 27582473,3-Difluoroazetidine hydrochlorideHCID 58075400HCID 58075400, compound

Product 1

HCID 58075837HCID 58075837, compoundYield 67.9%

Procedure

2,4-dichloro-8-(4-chlorophenyl)-7,8-dihydro-5H-pyrano[4,3-d]pyrimidine (Preparation K) (500 mg, 1.584 mmol) and 3,3-Difluoroazetidine hydrochloride (308 mg, 2.377 mmol) were combined and purified as per Preparation Ha to give 2-chloro-8-(4-chlorophenyl)-4-(3,3-difluoroazetidin-1-yl)-7,8-dihydro-5H-pyrano[4,3-d]pyrimidine (400 mg, 1.075 mmol, 67.8% yield) as a white solid. LC-MS (M+H)+=372.0. 1H NMR (500 MHz, CDCl3) δ ppm 7.22-7.34 (2 H, m), 7.12 (2 H, d, J=8.24 Hz), 4.63-4.85 (2 H, m), 4.46-4.64 (3 H, m), 4.04-4.17 (1 H, m), 3.91-4.04 (2 H, m).

Workup

  1. custompurified as per Preparation Ha

Sources & evidence

ORD record
ord-a0aa7cab8edd49abb0311607140b7a72
Source dataset
uspto-grants-2014_04
Patent number
US08710061B2

Reaction notes

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