Methanol → 5-Morpholin-4-yl-2-phenyl-imidazo[1,2-c]pyrimidin-7-ylamine

HRID 2382734Notes

Reaction equation

HRID 2382734 reaction equation
[N:1]1([C:7]2[N:12]=[C:11]([NH2:13])[CH:10]=[C:9]([NH2:14])[N:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.Br[CH2:16][C:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=O.C([O-])(O)=O.[Na+].CO>O>[N:1]1([C:7]2[N:8]3[CH:16]=[C:17]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[N:14]=[C:9]3[CH:10]=[C:11]([NH2:13])[N:12]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 887MethanolHCID 6259Phenacyl bromideHCID 516892Sodium BicarbonateHCID 143394012-(Morpholin-4-yl)pyrimidine-4,6-diamine

Product 1

HCID 670419775-Morpholin-4-yl-2-phenyl-imidazo[1,2-c]pyrimidin-7-ylamineYield 59.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-morpholin-4-yl-pyrimidine-4,6-diamine (1.0 g, 5.1 mmol), w-bromoacetophenone (1.02 g, 5.1 mmol), NaHCO3 (473 mg, 6 mmol) and methanol (15 ml) was heated under an atmosphere of argon to reflux (3 h). After cooling, water (10 ml) was added (the gummy precipitate could not be isolated). Methanol was evaporated, the residue was taken up in ethyl acetate, washed (water), and dried (Na2SO4). The solvent was evaporated and the title compound (900 mg, 50%) was isolated from the mixture by column chromatography (silica gel, heptane:ethyl acetate=80:20-60:40). MS (m/e)=296.3 [M+H+].

Workup

  1. temperaturewas heated under an atmosphere of argon
  2. temperatureto reflux (3 h)
  3. temperatureAfter cooling
  4. custombe isolated)
  5. customMethanol was evaporated
  6. washwashed (water)
  7. dry with materialdried (Na2SO4)
  8. customThe solvent was evaporated

Sources & evidence

ORD record
ord-c82ee18527244db391b15243fce1179a
Source dataset
uspto-grants-2012_09
Patent number
US08263584B2

Reaction notes

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