Toluene → HCID 54225089, compound

HRID 1858295Notes

Reaction equation

HRID 1858295 reaction equation
C([CH:5]([O:32][SiH:33]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH2:6][C:7]1[CH:8]=[C:9]([NH:13][C:14]2[C:19]([CH2:20][NH:21][C:22]3[C:27]([Cl:28])=[CH:26][CH:25]=[CH:24][C:23]=3[Cl:29])=[CH:18][N:17]=[C:16]([S:30][CH3:31])[N:15]=2)[CH:10]=[CH:11][CH:12]=1)(C)(C)C.C(N(CC)CC)C.[C:53](Cl)(Cl)=[O:54].[C:57]1([CH3:63])[CH:62]=CC=C[CH:58]=1>>[Si:33]([O:32][CH2:5][CH2:6][C:7]1[CH:8]=[C:9]([N:13]2[C:14]3=[N:15][C:16]([S:30][CH3:31])=[N:17][CH:18]=[C:19]3[CH2:20][N:21]([C:22]3[C:23]([Cl:29])=[CH:24][CH:25]=[CH:26][C:27]=3[Cl:28])[C:53]2=[O:54])[CH:10]=[CH:11][CH:12]=1)([C:57]([CH3:63])([CH3:62])[CH3:58])([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1

Participants

5

Reactant 4

HCID 1140Toluene3×HCID 6371PhosgeneHCID 8471TriethylamineHCID 178503453HCID 178503453, compound

Product 1

HCID 54225089HCID 54225089, compound

Procedure

A solution containing 1.35 g (2 mmol) of 4-[3-(2-tertbutyldiphenylsilyloxyethyl)phenyl]amino-5-(2,6-dichloroanilino)methyl-2-methylthiopyrimidine and 0.85 ml (6 mmol) of triethylamine in 5 ml of anhydrous toluene was added dropwise to 3.2 ml (6 mmol) of a 20% solution of phosgene in toluene dissolved in 10 ml of toluene at 0° C. under an atmosphere of nitrogen. The reaction was then heated at reflux for 6 hours then evaporated. The residue was partitioned between ethyl acetate (40 ml) and 2M hydrochloric acid (40 ml) and the ethyl acetate layer separated, washed with saturated aqueous sodium bicarbonate (40 ml ), dried over magnesium sulfate, filtered and evaporated to give 1.5 g of 1-[3-(2-t-butyldiphenylsilyloxyethyl)phenyl]-3-(2,6-dichlorophenyl)-7-methylthio-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one as a yellow gum. [Mass spectrum (ESI) MH+ =699].

Workup

  1. temperatureThe reaction was then heated
  2. temperatureat reflux for 6 hours
  3. customthen evaporated
  4. customThe residue was partitioned between ethyl acetate (40 ml) and 2M hydrochloric acid (40 ml)
  5. customthe ethyl acetate layer separated
  6. washwashed with saturated aqueous sodium bicarbonate (40 ml )
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-45f3b4b4f39e400b82198a7b11804569
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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