Bromotrimethylsilane → HCID 178491164, compound

HRID 1525222Notes

Reaction equation

HRID 1525222 reaction equation
[OH:1][C:2]1[C:7]([C:8]([NH:10][CH:11]([C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=2)[C:12]2[CH:13]=[C:14]([P:18](=[O:25])([O:22]CC)[O:19]CC)[CH:15]=[CH:16][CH:17]=2)=[O:9])=[CH:6][N:5]=[C:4]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=2)[N:3]=1.C[Si](Br)(C)C>ClCCl>[OH:1][C:2]1[C:7]([C:8]([NH:10][CH:11]([C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=2)[C:12]2[CH:13]=[C:14]([P:18](=[O:19])([OH:22])[OH:25])[CH:15]=[CH:16][CH:17]=2)=[O:9])=[CH:6][N:5]=[C:4]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=2)[N:3]=1

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 178476961HCID 178476961, compound2×

Product 1

HCID 178491164HCID 178491164, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of diethyl 3-((4-hydroxy-2-(pyridin-2-yl)pyrimidine-5-carboxamido)(4-methoxyphenyl)methyl)phenylphosphonate, 5-e, (0.99 g, 1.81 mmol) in dichloromethane (20 ml) was added TMSBr (5.6 g, 36.2 mmol) dropwise at 0° C. The resulting mixture was stirred at room temperature for 2 days. Then it was concentrated under vacuum and the residue was purified on prep-HPLC to provide the product, 5-1, (400 mg, 45%). 1H NMR (DMSO-d6, 300 MHz,): δ 8.80-8.82 (m, 1H), 8.37-8.40 (m, 1H,), 8.07-8.12 (m, 1H), 7.70-7.74 (m, 1H), 7.52-7.64 (m, 2H), 7.38-7.43 (m, 2H), 7.23-7.25 (m, 2H), 6.92-6.95 (m, 2H), 6.25-6.28 (m, 1H), 3.73 (s, 3H). (M−H)−=491.1.

Workup

  1. concentrationThen it was concentrated under vacuum
  2. customthe residue was purified on prep-HPLC
  3. customto provide the product, 5-1, (400 mg, 45%)

Sources & evidence

ORD record
ord-279bd6bf190c40dabbc0622e27f2e314
Source dataset
uspto-grants-2015_07
Patent number
US09079930B2

Reaction notes

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