Triethylamine → HCID 131722159, compound

HRID 1858274Notes

Reaction equation

HRID 1858274 reaction equation
Cl[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[S:9])=[CH:6][N:5]=[C:4]([CH3:13])[N:3]=1.C(N(CC)CC)C.[Si:21]([O:38][CH2:39][C:40]1[CH:41]=[C:42]([CH:44]=[CH:45][CH:46]=1)[NH2:43])([C:34]([CH3:37])([CH3:36])[CH3:35])([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>O1CCOCC1>[Si:21]([O:38][CH2:39][C:40]1[CH:41]=[C:42]([CH:44]=[CH:45][CH:46]=1)[NH:43][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[S:9])=[CH:6][N:5]=[C:4]([CH3:13])[N:3]=1)([C:34]([CH3:35])([CH3:36])[CH3:37])([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10044139HCID 10044139, compoundHCID 53249641Ethyl 4-chloro-2-methylthio-pyrimidine-5-carboxylate

Product 1

HCID 131722159HCID 131722159, compoundYield 103.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 2.32 g (10 mmol) of ethyl 4-chloro-2-methylthiopyrimidine-5-carboxylate in 30 ml of 1,4-dioxan was treated with 1.4 ml (10 mmol) of triethylamine and 4.7 g (13 mmol) of 3-(tert-butyldiphenylsilyloxymethyl)aniline. The mixture was heated to 50° C. for 18 hours and then evaporated. The residue was partitioned between 50 ml of ethyl acetate and 50 ml of 2M aqueous hydrochloric acid. The organic phase was dried over magnesium sulfate, filtered and evaporated to afford 5.6 g (100%) of ethyl 4-[3-(tert-butyldiphenylsilyloxymethyl)anilino]-2-methylthiopyrimidine-5-carboxylate as a colorless oil. [Mass spectrum (ESI) MH+ =558].

Workup

  1. customevaporated
  2. customThe residue was partitioned between 50 ml of ethyl acetate and 50 ml of 2M aqueous hydrochloric acid
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-12c32505fc994bd7a9618dcb25b61c30
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

Loading…