Ammonium Hydroxide → 8-(3,4-difluorophenyl)-7,8-dihydro-1H-pyrano[4,3-d]pyrimidine-2,4(3H,5H)-dione

HRID 2370192Notes

Reaction equation

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

Participants

Reactant 2

HCID 14923Ammonium Hydroxide

HCID 580758468-(3,4-difluorophenyl)-7,8-dihydropyrano[3,4-e][1,3]oxazine-2,4(3H,5H)-dione

Product 1

HCID 580755498-(3,4-difluorophenyl)-7,8-dihydro-1H-pyrano[4,3-d]pyrimidine-2,4(3H,5H)-dione

Procedure

8-(3,4-difluorophenyl)-7,8-dihydropyrano[3,4-e][1,3]oxazine-2,4(3H,5H)-dione (Intermediate Y(3)) was reacted as described in Intermediate X(4) with ammonium hydroxide to give 8-(3,4-difluorophenyl)-7,8-dihydro-1H-pyrano[4,3-d]pyrimidine-2,4(3H,5H)-dione (Intermediate Y(4)). LC-MS (M−H)+=279.1.

Sources & evidence

ORD record: ord-86a229f7f91b4bd19206b2d230fe75a1
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08710061B2

Reaction notes

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