[2-(Dimethylamino)pyrimidin-5-yl]boronic acid → 2-Amino-7-(2-dimethylamino-pyrimidin-5-yl)-[1,2,4]triazolo[1,5-a]pyridine-5-carboxylic acid hydrazide

HRID 2112951Notes

Reaction equation

HRID 2112951 reaction equation
C([O:3][C:4]([C:6]1[N:11]2[N:12]=[C:13]([NH2:15])[N:14]=[C:10]2[CH:9]=[C:8]([C:16]2[CH:17]=[N:18][C:19]([N:22]([CH3:24])[CH3:23])=[N:20][CH:21]=2)[CH:7]=1)=O)C.C(OC(C1[N:35]2[N:36]=C(N)N=C2C=C(Br)C=1)=O)C.CN(C)C1N=CC(B(O)O)=CN=1>>[NH2:15][C:13]1[N:14]=[C:10]2[CH:9]=[C:8]([C:16]3[CH:21]=[N:20][C:19]([N:22]([CH3:24])[CH3:23])=[N:18][CH:17]=3)[CH:7]=[C:6]([C:4]([NH:35][NH2:36])=[O:3])[N:11]2[N:12]=1

Participants

4

Reactant 3

HCID 45088929[2-(Dimethylamino)pyrimidin-5-yl]boronic acidHCID 576430722-Amino-7-bromo-[1,2,4]triazolo[1,5-a]pyridine-5-carboxylic acid ethyl esterHCID 576431482-Amino-7-(2-dimethylamino-pyrimidin-5-yl)-[1,2,4]triazolo[1,5-a]pyridine-5-carboxylic acid ethyl ester

Product 1

HCID 576431232-Amino-7-(2-dimethylamino-pyrimidin-5-yl)-[1,2,4]triazolo[1,5-a]pyridine-5-carboxylic acid hydrazide

Procedure

2-Amino-7-(2-dimethylamino-pyrimidin-5-yl)-[1,2,4]triazolo[1,5-a]pyridine-5-carboxylic acid ethyl ester, was prepared analogously to Example 28, Step 3, except 2-amino-7-bromo-[1,2,4]triazolo[1,5-a]pyridine-5-carboxylic acid ethyl ester (10.0 g, 35.1 mmol) was used as the starting material (which may be prepared as described in Example 6) and 2-dimethylamino-pyrimidin-5-boronic acid was used in place of 3-pyridyl-boronic acid to give 2-amino-7-(2-dimethylamino-pyrimidin-5-yl)-[1,2,4]triazolo[1,5-a]pyridine-5-carboxylic acid hydrazide. MS (APCI+): m/z 328.3.

Sources & evidence

ORD record
ord-7679afdfa2ba418080a8aa62250b9779
Source dataset
uspto-grants-2009_04
Patent number
US07524860B2

Reaction notes

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