2-Aminopyrimidine-5-boronic acid, pinacol ester → 5-(4,5-Dihydrobenzo[b]thieno[2,3-d]oxepin-2-yl)pyrimidin-2-amine

HRID 84472Notes

Reaction equation

HRID 84472 reaction equation
Br[C:2]1[S:15][C:5]2[C:6]3[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=3[O:8][CH2:9][CH2:10][C:4]=2[CH:3]=1.[NH2:16][C:17]1[N:22]=[CH:21][C:20](B2OC(C)(C)C(C)(C)O2)=[CH:19][N:18]=1>>[S:15]1[C:5]2[C:6]3[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=3[O:8][CH2:9][CH2:10][C:4]=2[CH:3]=[C:2]1[C:20]1[CH:19]=[N:18][C:17]([NH2:16])=[N:22][CH:21]=1

Participants

3

Reactant 2

HCID 177502122-Aminopyrimidine-5-boronic acid, pinacol esterHCID 579002002-Bromo-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine

Product 1

HCID 442424965-(4,5-Dihydrobenzo[b]thieno[2,3-d]oxepin-2-yl)pyrimidin-2-amine

Procedure

2-Bromo-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine was reacted with 2-aminopyrimidine-5-boronic acid pinacol ester using standard Suzuki coupling procedure. Purification on silica and triturating with diethyl ether gave 163. 1H NMR (400 MHz, CDCl3), 3.26 (2H, t, J=5.14), 4.37 (2H, t, J=5.18), 5.16 (2H, Broad s), 7.02-7.09 (3H, m), 7.16-7.22 (1H, m), 7.70 (1H, d, J=7.91), 8.56 (2H, s). MS: (ESI+) 396

Workup

  1. customPurification on silica
  2. customtriturating with diethyl ether

Sources & evidence

ORD record
ord-71ccc134b4b340db891dfc054e09a143
Source dataset
uspto-grants-2014_09
Patent number
US08846762B2

Reaction notes

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