Morpholine → HCID 13869556, compound

HRID 1903084Notes

Reaction equation

HRID 1903084 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[C:4]([N:16]2[CH2:21][CH2:20][N:19]([C:22]3[CH:27]=[CH:26][N:25]=[C:24](Cl)[N:23]=3)[CH2:18][CH2:17]2)[N:3]=1.[NH:29]1[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1>C(O)CCC>[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[C:4]([N:16]2[CH2:21][CH2:20][N:19]([C:22]3[CH:27]=[CH:26][N:25]=[C:24]([N:29]4[CH2:34][CH2:33][O:32][CH2:31][CH2:30]4)[N:23]=3)[CH2:18][CH2:17]2)[N:3]=1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 13869569HCID 13869569, compound

Product 1

HCID 13869556HCID 13869556, compoundYield 35.4%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

4-Amino-6,7-dimethoxy-2-[4-(2-chloropyrimidin-4-yl)-piperazino]quinazoline (2.0 g, 5.0 mmole) and morpholine (1.1 g, 12.6 mmole) in n-butanol (150 ml) were heated in a bomb at 160° C. for 19 hours. The solvent was evaporated in vacuo and the residue partitioned between 5% methanol in chloroform and 5 N sodium hydroxide solution. The organic layer was separated, washed with water, dried (Na2SO4) and evaporated in vacuo. The residue was chromatographed on silica gel (20 g, "Kieselgel" (Trade Mark) 60H) eluting with chloroform. Appropriate fractions were combined and evaporated in vacuo. Crystallization from ethyl acetate gave 0.8 g of the desired product, m.p. 232°-233° C.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue partitioned between 5% methanol in chloroform and 5 N sodium hydroxide solution
  3. customThe organic layer was separated
  4. washwashed with water
  5. dry with materialdried (Na2SO4)
  6. customevaporated in vacuo
  7. customThe residue was chromatographed on silica gel (20 g, "Kieselgel" (Trade Mark) 60H)
  8. washeluting with chloroform
  9. customevaporated in vacuo
  10. customCrystallization from ethyl acetate

Sources & evidence

ORD record
ord-048c51d04ca1461499d55193b7883ffe
Source dataset
uspto-grants-1984_03
Patent number
US04435401

Reaction notes

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