Nitroxyl → HCID 60141066, compound

HRID 1946930Notes

Reaction equation

HRID 1946930 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([F:17])=[C:6]([C:8]2([CH3:16])[N:13]=[C:12](OC)[CH2:11][O:10][CH2:9]2)[CH:7]=1.[N:18]1[CH:23]=[C:22](B(O)O)[CH:21]=[N:20][CH:19]=1.[NH:27]=O.[Cl-].[NH4+]>[Pd]>[F:17][C:5]1[CH:4]=[CH:3][C:2]([C:22]2[CH:23]=[N:18][CH:19]=[N:20][CH:21]=2)=[CH:7][C:6]=1[C:8]1([CH3:16])[CH2:9][O:10][CH2:11][C:12]([NH2:27])=[N:13]1

Participants

6

Reactant 4

HCID 945NitroxylHCID 25517Ammonium ChlorideHCID 2795193(Pyrimidin-5-yl)boronic acidHCID 68153507HCID 68153507, compound

Product 1

HCID 60141066HCID 60141066, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

In close analogy to the reaction sequence described in Example 31 (method B), the palladium-catalyzed coupling of (RS)-3-(5-bromo-2-fluoro-phenyl)-5-methoxy-3-methyl-3,6-dihydro-2H-[1,4]oxazine (intermediate XI-2) with pyrimidine-5-boronic acid followed by the treatment of the corresponding imino-ether with ammonium chloride yielded the 5-(2-fluoro-5-pyrimidin-5-yl-phenyl)-5-methyl-5,6-dihydro-2H-[1,4]oxazin-3-ylamine as a white foam. MS (ISP): m/z=302.2 [M+H]+.

Sources & evidence

ORD record
ord-b6dbd95a95b64d6592d6f80e77c53409
Source dataset
uspto-grants-2013_03
Patent number
US08399459B2

Reaction notes

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