N-bromobutanimide → HCID 66719218, compound

HRID 2280190Notes

Reaction equation

HRID 2280190 reaction equation
[CH:1]([N:4]1[CH:12]=[N:11][C:10]2[C:5]1=[N:6][C:7]([N:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1)=[N:8][C:9]=2[C:13]1[CH:14]=[N:15][C:16]([NH2:19])=[N:17][CH:18]=1)([CH3:3])[CH3:2].C1C(=O)N([Br:33])C(=O)C1>C(Cl)(Cl)Cl>[Br:33][C:12]1[N:4]([CH:1]([CH3:3])[CH3:2])[C:5]2[C:10]([N:11]=1)=[C:9]([C:13]1[CH:14]=[N:15][C:16]([NH2:19])=[N:17][CH:18]=1)[N:8]=[C:7]([N:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1)[N:6]=2

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 70224122HCID 70224122, compound

Product 1

HCID 66719218HCID 66719218, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 5-(9-isopropyl-2-morpholin-4-yl-9H-purin-6-yl)-pyrimidin-2-ylamine, (1.03 g, 3.03 mmol) in 15 ml of chloroform, was added slowly NBS (594 mg, 3.34 mmol) at a temperature of 5° C. The reaction was continued for 2 h at this temperature. After simple work-up, the product 5-(8-bromo-9-isopropyl-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 5-(8-bromo-9-isopropyl-2-morpholin-4-yl-9H-purin-6-yl)-pyrimidin-2-ylamine in a yield of 52% (660 mg). 1H NMR, MeOD: 9.67 (s, 2H), 4.90 (m, 1H), 3.89 (m, 4H), 3.82 (s, 4H), 1.72 (d, 6H). m/z: 419.31, 421.07 [MH]+.

Workup

  1. customAfter simple work-up, the product 5-(8-bromo-9-isopropyl-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-e9cb1f46ff27422d80cab1a5bbdad4fd
Source dataset
uspto-grants-2015_09
Patent number
US09138437B2

Reaction notes

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