Ammonium Chloride → {3-[5-(2-Morpholin-4-ylethoxy)pyrimidin-2-yl]phenyl}methanol

HRID 330799Notes

Reaction equation

HRID 330799 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[N:11]1([CH2:17][CH2:18][O:19][C:20]2[CH:21]=[N:22][C:23]([C:26]3[CH:27]=[C:28]([CH:33]=[CH:34][CH:35]=3)[C:29](OC)=[O:30])=[N:24][CH:25]=2)[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1.[Cl-].[NH4+]>C1COCC1>[N:11]1([CH2:17][CH2:18][O:19][C:20]2[CH:25]=[N:24][C:23]([C:26]3[CH:27]=[C:28]([CH2:29][OH:30])[CH:33]=[CH:34][CH:35]=3)=[N:22][CH:21]=2)[CH2:12][CH2:13][O:14][CH2:15][CH2:16]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 21225700DiisobutylaluminumhydrideHCID 58496335Methyl 3-[5-(2-morpholin-4-ylethoxy)pyrimidin-2-yl]benzoate

Product 1

HCID 58289758{3-[5-(2-Morpholin-4-ylethoxy)pyrimidin-2-yl]phenyl}methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

138 ml of a 1 M solution of diisobutylaluminium hydride in THF are added dropwise with stirring to a solution, kept under nitrogen, of 9.5 g (27.5 mmol) of methyl 3-[5-(2-morpholin-4-ylethoxy)pyrimidin-2-yl]benzoate in 180 ml of THF. After the mixture has been stirred at room temperature for 1 hour, 100 ml of a saturated aqueous ammonium chloride solution are added dropwise. The precipitate formed is filtered off with suction and washed a number of times with dichloromethane. The filtrate is dried over sodium sulfate and evaporated. The residue is recrystallised from a mixture of isopropanol/ether: {3-[5-(2-morpholin-4-ylethoxy)pyrimidin-2-yl]phenyl}-methanol as yellow crystals; m.p. 101-102°; ESI 316 (M+H); HPLC: Rt.=1.67 min (method A).

Workup

  1. stirringAfter the mixture has been stirred at room temperature for 1 hour
  2. customThe precipitate formed
  3. filtrationis filtered off with suction
  4. washwashed a number of times with dichloromethane
  5. dry with materialThe filtrate is dried over sodium sulfate
  6. customevaporated
  7. customThe residue is recrystallised from a mixture of isopropanol/ether
  8. custom=1.67 min (method A)

Sources & evidence

ORD record
ord-c9a5f7f350f849caa743a26503777f51
Source dataset
uspto-grants-2014_11
Patent number
US08877751B2

Reaction notes

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