3-(1,3-Dimethyl-2,4-dioxo-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyrimidin-5-yl)benzonitrile → 5-(3-fluorophenyl)-1,3-dimethyl-2,4-dioxo-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyrimidine-7-carbaldehyde

HRID 2201313Notes

Reaction equation

HRID 2201313 reaction equation
[CH3:1][N:2]1[C:7]2=[C:8]([CH:17]=[O:18])[NH:9][C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[C:6]2[C:5](=[O:19])[N:4]([CH3:20])[C:3]1=[O:21].[F:22]C1C=C(C2NC=C3C=2C(=O)N(C)C(=O)N3C)C=CC=1.CN1C2=CNC(C3C=C(C=CC=3)C#N)=C2C(=O)N(C)C1=O>>[F:22][C:13]1[CH:12]=[C:11]([C:10]2[NH:9][C:8]([CH:17]=[O:18])=[C:7]3[C:6]=2[C:5](=[O:19])[N:4]([CH3:20])[C:3](=[O:21])[N:2]3[CH3:1])[CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 3

HCID 867229283-(1,3-Dimethyl-2,4-dioxo-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyrimidin-5-yl)benzonitrileHCID 867229305-(3-fluorophenyl)-1,3-dimethyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dioneHCID 867235421,3-Dimethyl-2,4-dioxo-5-phenyl-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyrimidine-7-carbaldehyde

Product 1

HCID 867234965-(3-fluorophenyl)-1,3-dimethyl-2,4-dioxo-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyrimidine-7-carbaldehyde

Procedure

The title compound was prepared in a similar manner to 1,3-dimethyl-2,4-dioxo-5-phenyl-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyrimidine-7-carbaldehyde (Intermediate Na), starting from 5-(3-fluorophenyl)-1,3-dimethyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione (prepared in a similar manner to 3-(1,3-dimethyl-2,4-dioxo-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyrimidin-5-yl)benzonitrile (Example 9.0 Step 4) using the appropriate halo compound in step 3 and omitting Step 1.

Sources & evidence

ORD record
ord-25ca0b08b8784e3fab14eef6e6bced4e
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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