Bromotrimethylsilane → HCID 178462105, compound

HRID 1525214Notes

Reaction equation

HRID 1525214 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 178476964HCID 178476964, compound

Product 1

HCID 178462105HCID 178462105, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of diethyl (S)-4-(1-(4-hydroxy-2-(pyridin-2-yl)pyrimidine-5-carboxamido)ethyl)phenylphosphonate, 3-6, (400 mg, 0.88 mmol) in DCM (10 ml) was added dropwisely TMSBr (2.0 g, 13.15 mmol) at 0° C. 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 give the product, 3-7, (200 mg). 1H NMR (DMSO-d6, 300 MHz,): δ 10.71 (s, 4H), 9.93-9.96 (m, 1H), 8.80-8.81 (m, 1H), 8.56 (s, 1H), 8.37-8.39 (m, 1H), 8.08-8.13 (m, 1H), 7.61-7.74 (m, 3H), 7.42-7.46 (m, 2H), 5.12-5.17 (t, 1H), 2.07 (s, 1H), 1.49-1.51 (d, 3H).

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 give the product, 3-7, (200 mg)

Sources & evidence

ORD record
ord-965ac1b279e4492ba411dd2815b2569b
Source dataset
uspto-grants-2015_07
Patent number
US09079930B2

Reaction notes

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