Chlorotrimethylsilane → HCID 18506514, compound

HRID 1355322Notes

Reaction equation

HRID 1355322 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[C:8]([OH:15])[CH:7]=1.C[Si](Cl)(C)C.Br[C:22]1[N:27]=[CH:26][CH:25]=[CH:24][N:23]=1.[SiH3]Cl>O1CCOCC1>[OH:15][C:8]1[CH:7]=[C:6]([O:5][CH2:4][CH2:3][NH:2][C:22]2[N:27]=[CH:26][CH:25]=[CH:24][N:23]=2)[CH:14]=[CH:13][C:9]=1[C:10]([OH:12])=[O:11]

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 61622ChlorosilaneHCID 783452-BromopyrimidineHCID 131723943HCID 131723943, compound

Product 1

HCID 18506514HCID 18506514, compoundYield 65.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of compound (14) (20 g), dissopropylethylamine (74 mL), trimethylsilylchloride (21.6 mL) and 2-bromopyrimidine (Lancaster, 13.5 g) were combined in 350 mL 1,4-dioxane at room temperature, then brought to reflux under N2 atmosphere. After 2 days, an additional 12 mL silylchloride was added, and the mixture continued at reflux for an additional 2 days (until TLC showed no starting material remained). The reaction mixture was cooled to ambient temperature, concentrated to dryness in vacuo on a rotary evaporator and the residue suspended in water. The heterogeneous mixture was refluxed briefly, allowed to cool to room temperature, the product collected on a vacuum filter and air dried to give 15.3 g of (16), as a tan powder. NMR (400 MHz, DMSO-d6) d 12 (very broad, 2H) 8.3 (d, J=5 Hz, 2H) 7.7 (d, J=9 Hz, 1H), 7.28 (t, J=6 Hz, 1H), 6.57 (t, J=5 Hz, 1H), 6.49 (m, 2H), 4.13 (t, J=6 Hz, 2H), 3.62 (q, 2H); MS (+ESI) m/z 276 (M+H)+; IR (KBr) n (cm−1) 3275, 3000, 1660, 1625.

Workup

  1. temperatureto reflux under N2 atmosphere
  2. temperatureat reflux for an additional 2 days (until TLC
  3. concentrationconcentrated to dryness in vacuo on a rotary evaporator
  4. temperatureThe heterogeneous mixture was refluxed briefly
  5. temperatureto cool to room temperature
  6. customthe product collected on a vacuum
  7. filtrationfilter
  8. customair dried

Sources & evidence

ORD record
ord-242c901ae63140ab838b8a9db9a54003
Source dataset
uspto-grants-2003_07
Patent number
US06586187B1

Reaction notes

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