Triethylamine → [(S)-1-(2,6-Dichloro-5-methoxy-pyrimidin-4-yl)-pyrrolidin-2-yl]-methanol

HRID 334142Notes

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.[NH:12]1[CH2:16][CH2:15][CH2:14][C@H:13]1[CH2:17][OH:18].C(N(CC)CC)C>>[Cl:1][C:2]1[N:3]=[C:4]([N:12]2[CH2:16][CH2:15][CH2:14][C@H:13]2[CH2:17][OH:18])[C:5]([O:9][CH3:10])=[C:6]([Cl:8])[N:7]=1

Participants

Reactant 3

HCID 8471Triethylamine

HCID 640091L-Prolinol

HCID 202711362,4,6-Trichloro-5-methoxypyrimidine

Product 1

HCID 86667360[(S)-1-(2,6-Dichloro-5-methoxy-pyrimidin-4-yl)-pyrrolidin-2-yl]-methanolYield 70%

Procedure

A mixture of 2,4,6-trichloro-5-methoxy-pyrimidine (1.2 g, 5.62 mmol), (S)-1-pyrrolidin-2-yl-methanol (1.1 mL, 11.3 mmol) and triethylamine (1.08 mL, 7.75 mmol) in IMS (36 mL) was stirred at RT for 20 mins, then concentrated in vacuo. The resulting residue was purified by column chromatography (SiO2, 0 to 50% ethyl acetate in cyclohexane) affording [(S)-1-(2,6-Dichloro-5-methoxy-pyrimidin-4-yl)-pyrrolidin-2-yl]-methanol (1.08 mg, 70%). LCMS (method A): RT=2.98 min, [M+H]+=278/280.

Workup

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

Sources & evidence

ORD record: ord-6751090918cd4b95a17335f90c3bbd20
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08883799B2

Reaction notes

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