5-Bromo-2-iodopyrimidine → 5-Methanesulfonyl-2-(4-{5-methyl-4-[2-(2-methyl-pyrrolidin-1-yl)-ethyl]-oxazol-2-yl}-phenyl)-pyrimidine

HRID 1445834Notes

Reaction equation

HRID 1445834 reaction equation
CS([C:5]1[CH:10]=[CH:9][C:8](I)=[CH:7][N:6]=1)(=O)=O.BrC1C=CC(C2OC(C)=C(CC[O:26][S:27]([CH3:30])(=O)=[O:28])N=2)=CC=1.[CH3:32][C:33]1[O:37][C:36]([C:38]2[CH:43]=[CH:42][C:41](B3OC(C)(C)C(C)(C)O3)=[CH:40][CH:39]=2)=[N:35][C:34]=1[CH2:53][CH2:54]O.Br[C:57]1[CH:58]=[N:59][C:60](I)=[N:61][CH:62]=1>>[CH3:30][S:27]([C:57]1[CH:58]=[N:59][C:60]([C:41]2[CH:40]=[CH:39][C:38]([C:36]3[O:37][C:33]([CH3:32])=[C:34]([CH2:53][CH2:54][N:6]4[CH2:7][CH2:8][CH2:9][CH:10]4[CH3:5])[N:35]=3)=[CH:43][CH:42]=2)=[N:61][CH:62]=1)(=[O:28])=[O:26]

Participants

5

Reactant 4

HCID 70066515-Bromo-2-iodopyrimidineHCID 11451238Methanesulfonic acid 2-[2-(4-bromo-phenyl)-5-methyl-oxazol-4-yl]-ethyl esterHCID 589514312-{5-Methyl-2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]-oxazol-4-yl}-ethanol2×HCID 589514522-Methanesulfonyl-5-iodo-pyridine

Product 1

HCID 687000225-Methanesulfonyl-2-(4-{5-methyl-4-[2-(2-methyl-pyrrolidin-1-yl)-ethyl]-oxazol-2-yl}-phenyl)-pyrimidine

Procedure

The titled compound is prepared in substantial accordance with the procedures found in Example 4, Intermediate 33, Intermediate 13, and Example 75 using 2-{5-Methyl-2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]-oxazol-4-yl}-ethanol (see Intermediate 3) and 5-bromo-2-iodo-pyrimidine. MS (m/e): 427.3 (M+1)

Sources & evidence

ORD record
ord-5169b8ddcdf84121aeb9db192b9dfa9e
Source dataset
uspto-grants-2010_02
Patent number
US07666871B2

Reaction notes

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