Triethylamine → [4-(2,6-Dichloro-5-methoxy-pyrimidin-4-yl)-morpholin-3-yl]-methanol

HRID 334137Notes

Reaction equation

HRID 334137 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([O:9][CH3:10])=[C:4](Cl)[N:3]=1.Cl.[NH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH:14]1[CH2:19][OH:20].C(N(CC)CC)C>>[Cl:1][C:2]1[N:3]=[C:4]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH:14]2[CH2:19][OH:20])[C:5]([O:9][CH3:10])=[C:6]([Cl:8])[N:7]=1

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 202711362,4,6-Trichloro-5-methoxypyrimidineHCID 22342713(Morpholin-3-yl)methanol hydrochloride

Product 1

HCID 86667356[4-(2,6-Dichloro-5-methoxy-pyrimidin-4-yl)-morpholin-3-yl]-methanolYield 45%

Procedure

A mixture of 2,4,6-trichloro-5-methoxy-pyrimidine (1 g, 4.68 mmol), morpholin-3-yl-methanol hydrochloride (0.86 g, 5.6 mmol) and triethylamine (0.9 mL, 6.5 mmol) in IMS (30 mL) was stirred at RT for 3 h, then concentrated in vacuo. The resulting residue was purified by column chromatography (SiO2, 0 to 50% ethyl acetate in cyclohexane) affording [4-(2,6-Dichloro-5-methoxy-pyrimidin-4-yl)-morpholin-3-yl]-methanol (614 mg, 45%). LCMS (method A): RT=2.63 min, [M+H]+=294/296.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe resulting residue was purified by column chromatography (SiO2, 0 to 50% ethyl acetate in cyclohexane)

Sources & evidence

ORD record
ord-3353777918d5437c95a7ff2a792551e3
Source dataset
uspto-grants-2014_11
Patent number
US08883799B2

Reaction notes

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