Phosphorus oxide (P4O10) → HCID 44595336, compound

HRID 709400Notes

Reaction equation

HRID 709400 reaction equation
[CH3:1][Si:2]([C:5]#[C:6][C:7]1[C:8](=[O:14])[NH:9][C:10](=[O:13])[NH:11][CH:12]=1)([CH3:4])[CH3:3].O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.Br[CH:30]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>CC#N.Cl[Si](C)(C)C>[CH:30]([N:11]1[CH:12]=[C:7]([C:6]#[C:5][Si:2]([CH3:3])([CH3:4])[CH3:1])[C:8](=[O:14])[NH:9][C:10]1=[O:13])([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

6

Reactant 3

HCID 14812Phosphorus oxide (P4O10)HCID 236603BromodiphenylmethaneHCID 127820375-((trimethylsilyl)ethynyl)pyrimidine-2,4(1H,3H)-dione

Product 1

HCID 44595336HCID 44595336, compound

Reagents, catalysts & solvents 2

HCID 6397ChlorotrimethylsilaneCatalystHCID 6342AcetonitrileSolvent

Procedure

2.09 g (10 mmol) 5-TMSU (5-trimethylsilanylethynyluracil) dried over P4O10 are suspended in about 50 mL absolute MeCN, then 6 mL (25 mmol) BSA and a few drops of chlorotrimethylsilane are added via a septum, and the suspension is stirred at room temperature under argon until it is completely clear. Then 2.72 g (11 mmol) 1-bromodiphenylmethane are added to the resulting solution. The batch is now stirred for 24 h on an oil bath under exclusion from moisture at 84° C. The dark brown solution is concentrated and left to stand in the ice bath. The brown raw product that precipitates is separated, washed with a little cold MeCN, and recrystallized from about 50 mL MeCN.

Workup

  1. stirringThe batch is now stirred for 24 h on an oil bath under exclusion from moisture at 84° C
  2. concentrationThe dark brown solution is concentrated
  3. waitleft
  4. customThe brown raw product that precipitates
  5. customis separated
  6. washwashed with a little cold MeCN
  7. customrecrystallized from about 50 mL MeCN

Sources & evidence

ORD record
ord-aeb82489c84a44028dd8506fcb8daeba
Source dataset
uspto-grants-2015_11
Patent number
US09181199B2

Reaction notes

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