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

HRID 451107Notes

Reaction equation

HRID 451107 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]=[C:6]([F:8])[CH:7]=1.[OH-].[NH4+:22]>>[N:22]#[N:15].[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]=[C:6]([F:8])[CH:7]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 580753768-(3,5-difluorophenyl)-7,8-dihydropyrano[3,4-e][1,3]oxazine-2,4(3H,5H)-dione

Product 2

HCID 947NitrogenHCID 580754748-(3,5-difluorophenyl)-7,8-dihydro-1H-pyrano[4,3-d]pyrimidine-2,4(3H,5H)-dioneYield 166.7%

Conditions

Temperature
80 °C

Procedure

The mixture of 8-(3,5-difluorophenyl)-7,8-dihydropyrano[3,4-e][1,3]oxazine-2,4(3H,5H)-dione (Preparation X3)(230 mg, 0.818 mmol) and ammonium hydroxide (2229 mL, 57.3 mmol) in a sealed bottle was heated at 80° C. for 4 h. Blowed by N2 overnight to get 8-(3,5-difluorophenyl)-7,8-dihydro-1H-pyrano[4,3-d]pyrimidine-2,4(3H,5H)-dione (191 mg, 0.682 mmol, 83% yield) which was used as is. LC-MS (M+H)+=281.1.

Sources & evidence

ORD record
ord-1e938b335a5a47e78908512f445190e1
Source dataset
uspto-grants-2013_07
Patent number
US08486952B2

Reaction notes

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