Quinoline-3-boronic acid → 2-Chloro-7-(quinolin-3-yl)thieno[3,2-d]pyrimidin-4-amine

HRID 1485500Notes

Reaction equation

HRID 1485500 reaction equation
Br[C:2]1[C:6]2[N:7]=[C:8]([Cl:12])[N:9]=[C:10]([NH2:11])[C:5]=2[S:4][CH:3]=1.[N:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[C:15](B(O)O)[CH:14]=1>>[Cl:12][C:8]1[N:9]=[C:10]([NH2:11])[C:5]2[S:4][CH:3]=[C:2]([C:15]3[CH:14]=[N:13][C:22]4[C:17]([CH:16]=3)=[CH:18][CH:19]=[CH:20][CH:21]=4)[C:6]=2[N:7]=1

Participants

3

Reactant 2

HCID 2734663Quinoline-3-boronic acidHCID 866756507-Bromo-2-chlorothieno[3,2-d]pyrimidin-4-amine

Product 1

HCID 866756572-Chloro-7-(quinolin-3-yl)thieno[3,2-d]pyrimidin-4-amineYield 43.8%

Procedure

The target compound (260 mg, 43% yield) was prepared in the same manner as Step 1 of Example 11 using 7-bromo-2-chlorothieno[3,2-d]pyrimidin-4-amine (500 mg, 1.90 mmol) and quinolin-3-ylboronic acid (329 mg, 1.90 mmol).

Sources & evidence

ORD record
ord-ebb48133a35f447dac16486a9e591546
Source dataset
uspto-grants-2016_08
Patent number
US09422307B2

Reaction notes

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