N-bromobutanimide → HCID 25256169, compound

HRID 886821Notes

Reaction equation

HRID 886821 reaction equation
[CH:1]([N:5]1[CH:13]=[N:12][C:11]2[C:6]1=[N:7][C:8]([N:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1)=[N:9][C:10]=2[C:14]1[CH:15]=[N:16][C:17]([NH2:20])=[N:18][CH:19]=1)([CH2:3][CH3:4])[CH3:2].C1C(=O)N([Br:34])C(=O)C1>C(Cl)(Cl)Cl>[Br:34][C:13]1[N:5]([CH:1]([CH2:3][CH3:4])[CH3:2])[C:6]2[C:11]([N:12]=1)=[C:10]([C:14]1[CH:15]=[N:16][C:17]([NH2:20])=[N:18][CH:19]=1)[N:9]=[C:8]([N:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1)[N:7]=2

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 25221828HCID 25221828, compound

Product 1

HCID 25256169HCID 25256169, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 5-(9-sec-Butyl-2-morpholin-4-yl-9H-purin-6-yl)-pyrimidin-2-ylamine, (200 mg, 0.57 mmol) in 15 ml of chloroform, was added slowly NBS, (120 mg, 0.68 mmol) at a temperature of 5° C. The reaction was continued for 2 hours at this temperature. After simple work-up, the product 5-(8-Bromo-9-sec-butyl-2-morpholin-4-yl-9H-purin-6-yl)-pyrimidin-2-ylamine was purified by flash column (solvent system: 50% ethyl acetate in hexane) to deliver the desired compound in a yield of 49% (120 mg).

Workup

  1. customAfter simple work-up, the product 5-(8-Bromo-9-sec-butyl-2-morpholin-4-yl-9H-purin-6-yl)-pyrimidin-2-ylamine was purified by flash column (solvent system: 50% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-b1730b5b718740298b9068d7551710ba
Source dataset
uspto-grants-2012_08
Patent number
US08247410B2

Reaction notes

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