2,4-Dichloroaniline → HCID 69710630, compound

HRID 392104Notes

Reaction equation

HRID 392104 reaction equation
Cl[C:2]1[C:3]2[CH2:13][N:12]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:11][CH2:10][C:4]=2[N:5]=[C:6]([S:8][CH3:9])[N:7]=1.[Cl:21][C:22]1[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:23]=1[NH2:24].C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>O1CCCC1>[Cl:21][C:22]1[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:23]=1[NH:24][C:2]1[C:3]2[CH2:13][N:12]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:11][CH2:10][C:4]=2[N:5]=[C:6]([S:8][CH3:9])[N:7]=1

Participants

5

Reactant 3

HCID 111232,4-DichloroanilineHCID 2724254Sodium bis(trimethylsilyl)amideHCID 86583989HCID 86583989, compound

Product 1

HCID 69710630HCID 69710630, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of tert-butyl 4-chloro-2-methylthio-5,6,7,8-tetrahydropyridino[4,3-d]pyrimidine-6-carboxylate (100 mg, 0.317 mmol), 2,4-dichloroaniline (56 mg, 0.348 mmol) and sodium bis(trimethylsilyl)amide (1.0 M solution in THF, 412 □l, 0.412 mmol) in tetrahydrofuran (2 ml) was heated at reflux over night. The mixture was partitioned between ethyl acetate and water. Organic layer was separated and washed with brine, dried (MgSO4) and filtered. Concentration of filtrate afforded crude product, which was purified by flash chromatography (0.5% methanol in dichloromethane as eluent) to give tert-butyl 4-[(2,4-dichlorophenyl)amino]-2-methylthio-5,6,7,8-tetrahydropyridino[4,3-d]pyrimidine-6-carboxylate as a light yellow oil (85 mg, yield 61%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux over night
  3. customThe mixture was partitioned between ethyl acetate and water
  4. customOrganic layer was separated
  5. washwashed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customConcentration of filtrate afforded crude product, which
  9. customwas purified by flash chromatography (0.5% methanol in dichloromethane as eluent)

Sources & evidence

ORD record
ord-f600c59e581d4bbb805b6634c15cbc49
Source dataset
uspto-grants-2004_10
Patent number
US06800632B2

Reaction notes

Loading…