Bromotrimethylsilane → HCID 178457729, compound

HRID 1525324Notes

Reaction equation

HRID 1525324 reaction equation
[OH:1][C:2]1[C:7]([C:8]([NH:10][C:11]([C:14]2[CH:15]=[CH:16][C:17]([C:20]3[CH:25]=[CH:24][C:23]([P:26](=[O:33])([O:30]CC)[O:27]CC)=[CH:22][CH:21]=3)=[N:18][CH:19]=2)([CH3:13])[CH3:12])=[O:9])=[CH:6][N:5]=[C:4]([C:34]2[N:35]=[N:36][CH:37]=[CH:38][CH:39]=2)[N:3]=1.C[Si](Br)(C)C>C(Cl)Cl>[OH:1][C:2]1[C:7]([C:8]([NH:10][C:11]([C:14]2[CH:15]=[CH:16][C:17]([C:20]3[CH:21]=[CH:22][C:23]([P:26](=[O:27])([OH:30])[OH:33])=[CH:24][CH:25]=3)=[N:18][CH:19]=2)([CH3:13])[CH3:12])=[O:9])=[CH:6][N:5]=[C:4]([C:34]2[N:35]=[N:36][CH:37]=[CH:38][CH:39]=2)[N:3]=1

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 178476956HCID 178476956, compound

Product 1

HCID 178457729HCID 178457729, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of diethyl 4-(5-(2-(4-hydroxy-2-(pyridazin-3-yl)pyrimidine-5-carboxamido) propan-2-yl)pyridin-2-yl)phenylphosphonate (180 mg, 0.33 mmol) in DCM (5 ml) was added dropwise TMSBr (1.50 g, 9.85 mmol) at 0° C., the reaction mixture was stirred at room temperature for overnight. Then evaporated the solution and diluted with 20 ml MeOH, and stirred at room temperature for 30 mins, concentrated under vacuo, purified by Pre-HPLC to give product 33-1. 1H NMR (CDCl3-d6, 300 MHz,): δ 9.50 (s, 1H), 8.71 (s, 1H), 8.50 (d, 1H), 8.11 (m, 2H), 7.72-8.02 (m, 5H), 3.15 (s, 1H), 1.76 (s, 6H). (M+H)+=493.1.

Workup

  1. customThen evaporated the solution
  2. additiondiluted with 20 ml MeOH
  3. stirringstirred at room temperature for 30 mins
  4. concentrationconcentrated under vacuo
  5. custompurified by Pre-HPLC

Sources & evidence

ORD record
ord-1ebf8ff204cc4c409aeb37644098d93f
Source dataset
uspto-grants-2015_07
Patent number
US09079930B2

Reaction notes

Loading…