1,5-Dioxa-9-azaspiro(5.5)undecane → 4-(7,11-Dioxa-3-azaspiro[5.5]undec-3-yl)-6-oxo-2-(3-thienylmethyl)-1,6-dihydropyrimidine-5-carbonitrile

HRID 414987Notes

Reaction equation

HRID 414987 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].[O:18]1[C:23]2([CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)[O:22][CH2:21][CH2:20][CH2:19]1>>[CH2:24]1[C:23]2([O:18][CH2:19][CH2:20][CH2:21][O:22]2)[CH2:28][CH2:27][N:26]([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])[CH2:25]1

Participants

3

Reactant 2

HCID 27372161,5-Dioxa-9-azaspiro(5.5)undecaneHCID 584079424-(Methylsulphanyl)-6-oxo-2-(3-thienylmethyl)-1,6-dihydropyrimidine-5-carbonitrile

Product 1

HCID 1359950424-(7,11-Dioxa-3-azaspiro[5.5]undec-3-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 597 mg (3.80 mmol) of 1,5-dioxa-9-azaspiro[5.5]undecane to give 86 mg (61% of theory) of the title compound.

Sources & evidence

ORD record
ord-c9215d1f464e451a813e703278e40fe7
Source dataset
uspto-grants-2012_01
Patent number
US08088769B2

Reaction notes

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