Piperidin-4-ol → 4-(4-Hydroxypiperidin-1-yl)-6-oxo-2-(3-thienylmethyl)-1,6-dihydropyrimidine-5-carbonitrile

HRID 414983Notes

Reaction equation

HRID 414983 reaction equation
CS[C:3]1[N:4]=[C:5]([CH2:12][C:13]2[CH:17]=[CH:16][S:15][CH:14]=2)[NH:6][C:7](=[O:11])[C:8]=1[C:9]#[N:10].[NH:18]1[CH2:23][CH2:22][CH:21]([OH:24])[CH2:20][CH2:19]1>>[OH:24][CH:21]1[CH2:22][CH2:23][N:18]([C:3]2[N:4]=[C:5]([CH2:12][C:13]3[CH:17]=[CH:16][S:15][CH:14]=3)[NH:6][C:7](=[O:11])[C:8]=2[C:9]#[N:10])[CH2:19][CH2:20]1

Participants

3

Reactant 2

HCID 79341Piperidin-4-olHCID 584079424-(Methylsulphanyl)-6-oxo-2-(3-thienylmethyl)-1,6-dihydropyrimidine-5-carbonitrile

Product 1

HCID 1359950614-(4-Hydroxypiperidin-1-yl)-6-oxo-2-(3-thienylmethyl)-1,6-dihydropyrimidine-5-carbonitrile

Procedure

In analogy to the preparation of Example 1, 100 mg (0.38 mmol) of 4-(methylsulphanyl)-6-oxo-2-(3-thienylmethyl)-1,6-dihydropyrimidine-5-carbonitrile are reacted with 384 mg (3.80 mmol) of piperidin-4-ol to give 47 mg (39% of theory) of the title compound.

Sources & evidence

ORD record
ord-d72a6fe3267041189e79da48036a3da9
Source dataset
uspto-grants-2012_01
Patent number
US08088769B2

Reaction notes

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