Ammonium Hydroxide → 4-(2,4-dioxo-2,3,4,5,7,8-hexahydro-1H-pyrano[4,3-d]pyrimidin-8-yl)benzonitrile

HRID 475836Notes

Reaction equation

[O:1]=[C:2]1[NH:7][C:6](=[O:8])[C:5]2[CH2:9][O:10][CH2:11][CH:12]([C:13]3[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=3)[C:4]=2O1.[OH-].[NH4+:22]>>[O:1]=[C:2]1[NH:22][C:4]2[CH:12]([C:13]3[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=3)[CH2:11][O:10][CH2:9][C:5]=2[C:6](=[O:8])[NH:7]1

Participants

Reactant 2

HCID 14923Ammonium Hydroxide

HCID 580754234-(2,4-Dioxo-2,3,4,5,7,8-hexahydropyrano[3,4-e][1,3]oxazin-8-yl)benzonitrile

Product 1

HCID 580754224-(2,4-dioxo-2,3,4,5,7,8-hexahydro-1H-pyrano[4,3-d]pyrimidin-8-yl)benzonitrile

Procedure

4-(2,4-dioxo-2,3,4,5,7,8-hexahydropyrano[3,4-e][1,3]oxazin-8-yl)benzonitrile (Intermediate AA(3)) was reacted as described in Intermediate X(4) with ammonium hydroxide to give 4-(2,4-dioxo-2,3,4,5,7,8-hexahydro-1H-pyrano[4,3-d]pyrimidin-8-yl)benzonitrile (Intermediate AA(4)). LC-MS (M−H)+=270.2.

Sources & evidence

ORD record: ord-67a7b3c5f3d04246a327b0715244fbac
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637525B2

Reaction notes

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