3-(Hydroxymethyl)cyclobutan-1-ol → HCID 178521633, compound

HRID 1020178Notes

Reaction equation

HRID 1020178 reaction equation
CS([C:5]1[N:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:7][N:6]=1)(=O)=O.[OH:19][CH2:20][CH:21]1[CH2:24][CH:23]([OH:25])[CH2:22]1>>[C:13]1([C:12]#[C:11][C:8]2[CH:7]=[N:6][C:5]([O:19][CH2:20][C@H:21]3[CH2:24][C@H:23]([OH:25])[CH2:22]3)=[N:10][CH:9]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

3

Reactant 2

HCID 140451763-(Hydroxymethyl)cyclobutan-1-olHCID 575167582-Methanesulfonyl-5-phenylethynyl-pyrimidine

Product 1

HCID 178521633HCID 178521633, compound

Procedure

The title compound, yellow solid, MS: m/e=281.1 (M+H+), can be prepared in accordance with the general method of example 1, step 3 from 2-methanesulfonyl-5-phenylethynyl-pyrimidine (example 1, step 2) and 3-(hydroxymethyl)cyclobutanol by using Cs2CO3 as base and dioxane as solvent for 16 hours at 100° C. and by separation of the received isomers-mixture using a chiral column (Lux2 Cellulose with heptane:isopropanol 85:15 as solvent).

Sources & evidence

ORD record
ord-f201c7b26b3e4c9f9ae2d257c3c2f8bb
Source dataset
uspto-grants-2014_05
Patent number
US08716316B2

Reaction notes

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