7-((4-chlorothiazol-2-yl)(hydroxy)methyl)-1,3-dimethyl-5-phenyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione → 7-((4-Chlorothiazol-2-yl)(hydroxy)methyl)-5-(3-fluorophenyl)-1,3-dimethyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

HRID 2201256Notes

Reaction equation

HRID 2201256 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([CH:7]([OH:27])[C:8]2[NH:9][C:10]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[C:11]3[C:16](=[O:17])[N:15]([CH3:18])[C:14](=[O:19])[N:13]([CH3:20])[C:12]=23)[S:5][CH:6]=1.[F:28]C1C=C(C2NC(C=O)=C3C=2C(=O)N(C)C(=O)N3C)C=CC=1.C(C1C=C(C2N(CCC(N(OC)C)=O)C=C3C=2C(=O)N(C)C(=O)N3C)C=CC=1)#N>>[Cl:1][C:2]1[N:3]=[C:4]([CH:7]([OH:27])[C:8]2[NH:9][C:10]([C:21]3[CH:22]=[CH:23][CH:24]=[C:25]([F:28])[CH:26]=3)=[C:11]3[C:16](=[O:17])[N:15]([CH3:18])[C:14](=[O:19])[N:13]([CH3:20])[C:12]=23)[S:5][CH:6]=1

Participants

4

Reactant 3

HCID 867234707-((4-chlorothiazol-2-yl)(hydroxy)methyl)-1,3-dimethyl-5-phenyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dioneHCID 867234965-(3-fluorophenyl)-1,3-dimethyl-2,4-dioxo-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyrimidine-7-carbaldehydeHCID 867234973-(5-(3-Cyanophenyl)-1,3-dimethyl-2,4-dioxo-3,4-dihydro-1H-pyrrolo[3,4-d]pyrimidin-6(2H)-yl)-N-methoxy-N-methylpropanamide2×

Product 1

HCID 867234957-((4-Chlorothiazol-2-yl)(hydroxy)methyl)-5-(3-fluorophenyl)-1,3-dimethyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

Procedure

The title compound was prepared by an analogous method to 7-((4-chlorothiazol-2-yl)(hydroxy)methyl)-1,3-dimethyl-5-phenyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione (Example 21 Step 1) from 5-(3-fluorophenyl)-1,3-dimethyl-2,4-dioxo-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyrimidine-7-carbaldehyde (Intermediate Nc) and 2-bromo-4-chlorothiazole (Intermediate Q, step 2);

Sources & evidence

ORD record
ord-04c4a1987190447794318d5d867afbf2
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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