2-Chloro-4,6-dimethylpyrimidine → 2-(2,6-Dimethylpyrimidin-4-yl)-5-{[5-fluoro-2-(2H-1,2,3-triazol-2-yl)phenyl]carbonyl}octahydropyrrolo[3,4-c]pyrrole

HRID 1525068Notes

Reaction equation

HRID 1525068 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:18]2[N:22]=[CH:21][CH:20]=[N:19]2)=[C:6]([C:8]([N:10]2[CH2:17][CH:16]3[CH:12]([CH2:13][NH:14][CH2:15]3)[CH2:11]2)=[O:9])[CH:7]=1.C(OC(N1CC2C(CNC2)C1)=O)(C)(C)C.Cl[C:39]1[CH:44]=[C:43]([CH3:45])[N:42]=[C:41]([CH3:46])[N:40]=1.ClC1N=C(C)C=C(C)N=1>CC(O)=O>[CH3:46][C:41]1[N:40]=[C:39]([N:14]2[CH2:13][CH:12]3[CH:16]([CH2:17][N:10]([C:8]([C:6]4[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=4[N:18]4[N:22]=[CH:21][CH:20]=[N:19]4)=[O:9])[CH2:11]3)[CH2:15]2)[CH:44]=[C:43]([CH3:45])[N:42]=1

Participants

6

Reactant 4

HCID 205502-Chloro-4,6-dimethylpyrimidineHCID 31541994-chloro-2,6-dimethylpyrimidineHCID 4142526Tert-butyl octahydropyrrolo(3,4-c)pyrrole-2-carboxylateHCID 67116387(5-Fluoro-2-[1,2,3]triazol-2-yl-phenyl)-(hexahydro-pyrrolo[3,4-c]pyrrol-2-yl)-methanone

Product 1

HCID 671162262-(2,6-Dimethylpyrimidin-4-yl)-5-{[5-fluoro-2-(2H-1,2,3-triazol-2-yl)phenyl]carbonyl}octahydropyrrolo[3,4-c]pyrrole

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The title compound was prepared in a manner analogous to Intermediate 23, substituting (5-fluoro-2-(2H-1,2,3-triazol-2-yl)phenyl)(hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)methanone (Intermediate 21) for hexahydro-pyrrolo[3,4-c]pyrrole-2-carboxylic acid tert-butyl ester and 4-chloro-2,6-dimethylpyrimidine for 2-chloro-4,6-dimethyl-pyrimidine in Step A. MS (ESI) mass calcd for C21H22FN7O, 407.19; m/z found, 408.2 [M+H]+.

Sources & evidence

ORD record
ord-8ed2c6b21270425fb0977e40b07c6eeb
Source dataset
uspto-grants-2015_07
Patent number
US09079911B2

Reaction notes

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