Triethylamine → HCID 86756057, compound

HRID 1858284Notes

Reaction equation

HRID 1858284 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.[O:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH:15]1[O:20][CH2:21][C:22]1[CH:28]=[CH:27][C:25]([NH2:26])=[CH:24][CH:23]=1.C(N(CC)CC)C>O1CCOCC1>[O:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH:15]1[O:20][CH2:21][C:22]1[CH:23]=[CH:24][C:25]([NH:26][C:2]2[C:7]([C:8]([O:10][CH2:11][CH3:12])=[S:9])=[CH:6][N:5]=[C:4]([CH3:13])[N:3]=2)=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 184721974-(2-Tetrahydropyranyloxymethyl)anilineHCID 53249641Ethyl 4-chloro-2-methylthio-pyrimidine-5-carboxylate

Product 1

HCID 86756057HCID 86756057, compoundYield 94.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 4.25 g (18.26 mmol) of ethyl 4-chloro-2-methylthio-pyrimidine-5-carboxylate, 4.73 g (22.85 mmol) of 4-(tetrahydropyran-2-yloxymethyl)aniline and 6.4 ml (45.7 mmol) of triethylamine in sieve-dried 1,4-dioxan was heated at 60° C. for 4 hours. The reaction mixture was evaporated and the residue partitioned between ethyl acetate and water. The ethyl acetate layer was separated, dried (MgSO4) and evaporated to give a brown oil which was purified by flash chromatography on silica gel using1:4 ethyl acetate/hexane as eluent. Product containing fractions were combined and evaporated to give 6.68 g (90%) of ethyl 4-[4-(tetrahydropyran-2-yloxymethyl)phenyl]amino-2-methylthiopyrimidine-5-carboxylate as a yellow oil. [Mass spectrum (ESI) MH+ =404].

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue partitioned between ethyl acetate and water
  3. customThe ethyl acetate layer was separated
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customto give a brown oil which
  7. customwas purified by flash chromatography on silica gel using1:4 ethyl acetate/hexane as eluent
  8. additionProduct containing fractions
  9. customevaporated

Sources & evidence

ORD record
ord-9d909b3466074baeb2fae98505f9658b
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

Loading…