Bromotrimethylsilane → HCID 178462104, compound

HRID 1525213Notes

Reaction equation

HRID 1525213 reaction equation
[OH:1][C:2]1[C:7]([C:8]([NH:10][C@@H:11]([C:13]2[CH:18]=[CH:17][C:16]([P:19](=[O:26])([O:23]CC)[O:20]CC)=[CH:15][CH:14]=2)[CH3:12])=[O:9])=[CH:6][N:5]=[C:4]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=2)[N:3]=1.C[Si](Br)(C)C>C(Cl)Cl>[OH:1][C:2]1[C:7]([C:8]([NH:10][C@@H:11]([C:13]2[CH:14]=[CH:15][C:16]([P:19](=[O:20])([OH:26])[OH:23])=[CH:17][CH:18]=2)[CH3:12])=[O:9])=[CH:6][N:5]=[C:4]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=2)[N:3]=1

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 178476963HCID 178476963, compound

Product 1

HCID 178462104HCID 178462104, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-diethyl 4-(1-(4-hydroxy-2-(pyridin-2-yl)pyrimidine-5-carboxamido)ethyl)phenylphosphonate, 3-4, (400 mg, 0.88 mmol) in DCM (10 ml) was added dropwise TMSBr (2.0 g, 13.15 mmol) at 0° C., and the reaction mixture was stirred at room temperature overnight. The reaction mixture was evaporated to dryness, and the residue was treated with MeCN and water at room temperature. The resulting solid was collected via filtration to obtain the product, 3-5, (200 mg). 1H NMR (DMSO-d6, 300 MHz,): δ 11.29 (s, 5H), 9.93-9.96 (m, 1H), 8.80-8.81 (m, 1H), 8.56 (s, 1H), 8.37-8.39 (m, 1H), 8.07-8.12 (m, 1H), 7.61-7.74 (m, 3H), 7.42-7.46 (m, 2H), 5.12-5.16 (m, 1H) 2.07 (s, 1H), 1.48-1.51 (m, 3H), (M+H)+=401.2.

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. additionthe residue was treated with MeCN and water at room temperature
  3. filtrationThe resulting solid was collected via filtration
  4. customto obtain the product, 3-5, (200 mg)

Sources & evidence

ORD record
ord-b6ac8ae40df1433c9d43ff27f42d7140
Source dataset
uspto-grants-2015_07
Patent number
US09079930B2

Reaction notes

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