Chlorosuccinimide → 7-chloro-6-(4-(6-fluoropyridin-2-yl)benzyl)-1-isobutyl-3-methyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

HRID 1422997Notes

Reaction equation

HRID 1422997 reaction equation
[F:1][C:2]1[N:7]=[C:6]([C:8]2[CH:30]=[CH:29][C:11]([CH2:12][N:13]3[CH:21]=[C:20]4[C:15]([N:16]([CH2:25][CH:26]([CH3:28])[CH3:27])[C:17](=[O:24])[N:18]([CH3:23])[C:19]4=[O:22])=[CH:14]3)=[CH:10][CH:9]=2)[CH:5]=[CH:4][CH:3]=1.[Cl:31]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.CN(C=O)C>[Cl:31][C:14]1[N:13]([CH2:12][C:11]2[CH:29]=[CH:30][C:8]([C:6]3[CH:5]=[CH:4][CH:3]=[C:2]([F:1])[N:7]=3)=[CH:9][CH:10]=2)[CH:21]=[C:20]2[C:19](=[O:22])[N:18]([CH3:23])[C:17](=[O:24])[N:16]([CH2:25][CH:26]([CH3:28])[CH3:27])[C:15]=12

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 674416686-(4-(6-fluoropyridin-2-yl)benzyl)-1-isobutyl-3-methyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

Product 1

HCID 686246447-chloro-6-(4-(6-fluoropyridin-2-yl)benzyl)-1-isobutyl-3-methyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dioneYield 70%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

6-(4-(6-fluoropyridin-2-yl)benzyl)-1-isobutyl-3-methyl-1H-pyrrolo [3,4-d]pyrimidine-2,4(3H,6H)-dione (81 mg, 0.2 mmol) is dissolved in a mixture of CCl4 and DMF (3/1, v/v), and then N-chlorosuccinimide (27 mg, 0.2 mmol) is added. The reaction mixture is heated in a Biotage microwave at 100° C. for 30 minutes. Solvents are removed under vacuum, and the residue is purified by a semi-preparative HPLC to give pure product as off white solids (50 mg, yield 70%). MS (ESI) m/z 441.2 [M+H]+.

Workup

  1. customSolvents are removed under vacuum
  2. customthe residue is purified by a semi-preparative HPLC

Sources & evidence

ORD record
ord-69c7c19241854353887c1dc1a40abdc6
Source dataset
uspto-grants-2015_01
Patent number
US08927556B2

Reaction notes

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