Sodium Hydroxide → HCID 59127749, compound

HRID 386411Notes

Reaction equation

[CH2:1]([N:8]1[CH:16]=[N:15][C:14]2[C:9]1=[N:10][C:11]([Cl:18])=[N:12][C:13]=2[NH2:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(=O)C.[Na+].[Br:24]Br.[O-]S([O-])(=S)=O.[Na+].[Na+].[OH-].[Na+]>C(O)(=O)C>[CH2:1]([N:8]1[C:16]([Br:24])=[N:15][C:14]2[C:9]1=[N:10][C:11]([Cl:18])=[N:12][C:13]=2[NH2:17])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 70 °C

Procedure

The product from Step 2 (3 g, 11.6 mmol) was suspended in acetic acid (50 mL) and sodium acetate (1.4 g, 17.3 mmol) and the mixture cooled in an ice bath while bromine (3.6 mL, 69.3 mmol) was added dropwise. After the addition was complete, the mixture was heated at 70° C. under a nitrogen atmosphere for 5 h and then allowed to cool to room temperature. The mixture was poured onto 50 mL of a 10% aqueous Na2S2O3 solution, and the whole reduced in vacuo to approximately 10 mL and then neutralized with 2 N NaOH solution. The organics were extracted with dichloromethane (3×150 mL), washed with water (100 mL) and brine (100 mL) and then dried (MgSO4) and evaporated to a yellow solid. Trituration of the solid with ether and filtration provided an off-white solid of 9-benzyl-8-bromo-2-chloro-9H-purin-6-ylamine (3.3 g, 85%) which was found to be sufficiently pure to be used with no further purification.

Workup

additionwas added dropwise
additionAfter the addition
temperatureto cool to room temperature
extractionThe organics were extracted with dichloromethane (3×150 mL)
washwashed with water (100 mL) and brine (100 mL)
dry with materialdried (MgSO4)
customevaporated to a yellow solid
filtrationTrituration of the solid with ether and filtration

Sources & evidence

ORD record: ord-6d88391d7d6a4ae99aec0c44b327e9b2
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08372836B2

Reaction notes

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