Diiodomethane → 2-[1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-6-iodo-7-methyl-7,9-dihydro-8H-purin-8-one

HRID 510130Notes

Reaction equation

HRID 510130 reaction equation
N[C:2]1[N:10]=[C:9]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[CH:17][CH:18]=3)[N:13]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[F:27])[N:12]=2)[N:8]=[C:7]2[C:3]=1[N:4]([CH3:29])[C:5](=[O:28])[NH:6]2.N(OCCC(C)C)=O.[I:38]CI>>[F:27][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[CH2:20][N:13]1[C:14]2=[N:15][CH:16]=[CH:17][CH:18]=[C:19]2[C:11]([C:9]2[N:8]=[C:7]3[C:3]([N:4]([CH3:29])[C:5](=[O:28])[NH:6]3)=[C:2]([I:38])[N:10]=2)=[N:12]1

Participants

4

Reactant 3

HCID 6346DiiodomethaneHCID 8053Isoamyl NitriteHCID 666141366-Amino-2-(1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl)-7-methyl-7H-purin-8(9H)-one

Product 1

HCID 867200522-[1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-6-iodo-7-methyl-7,9-dihydro-8H-purin-8-one

Conditions

Temperature
85 °C

Procedure

1.725 g (3.358 mmol) of the compound from example 41 were dissolved in 7 ml of diiodomethane and admixed with 7.19 ml (53.732 mmol) of isopentyl nitrite. The reaction mixture was heated to 85° C. for 16 h and, after cooling, concentrated on a rotary evaporator. The residue was by means of preparative HPLC (eluent: water/acetonitrile/water with 1% trifluoroacetic acid, gradient 55:40:5→0:95:5). 64 mg of the title compound were obtained (4% of theory).

Workup

  1. temperatureafter cooling
  2. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-115242ac24a746caa104d15fe95e32ff
Source dataset
uspto-grants-2015_08
Patent number
US09096592B2

Reaction notes

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