Water → HCID 178510560, compound

HRID 892118Notes

Reaction equation

HRID 892118 reaction equation
[CH2:1]([C@@H:8]1[CH2:19][N:18]2[C:10]([C:11]3[NH:12][C:13]([CH:21]4[CH2:25][CH2:24][CH2:23][CH2:22]4)=[N:14][C:15]=3[N:16]=[C:17]2Cl)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[C-:32]#[N:33].[K+].O>CN(C)C=O>[CH2:1]([C@@H:8]1[CH2:19][N:18]2[C:10]([C:11]3[NH:12][C:13]([CH:21]4[CH2:25][CH2:24][CH2:23][CH2:22]4)=[N:14][C:15]=3[N:16]=[C:17]2[C:32]#[N:33])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 9032Potassium CyanideHCID 10796Cesium carbonateHCID 178478320(8R)-8-benzyl-5-chloro-2-cyclopentyl-7,8-dihydro-1H-imidazo[2,1-f]purine

Product 1

HCID 178510560HCID 178510560, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Compound 67a (217 mg, 0.529 mmol) obtained in Example 67 was dissolved in N,N-dimethylformamide (4 mL), to the solution were added cesium carbonate (245 mg, 0.750 mmol, 1.5 equivalents) and potassium cyanide (39 mg, 0.600 mmol, 1.2 equivalents), and the mixture was stirred at 100° C. for 4 hours. To the reaction mixture was added water, and the deposited crystals were collected by filtration to obtain the title compound (125 mg, 73%) as a yellow solid.

Workup

  1. filtrationthe deposited crystals were collected by filtration

Sources & evidence

ORD record
ord-5c95402e114d4d7c895781214309889d
Source dataset
uspto-grants-2006_02
Patent number
US07005430B2

Reaction notes

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