Tetrabutylammonium Fluoride → HCID 44819302, compound

HRID 2359614Notes

Reaction equation

HRID 2359614 reaction equation
[CH3:1][N:2]([CH3:20])[C:3]([C:5]1[N:14]([CH:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)[C:8]2[N:9]=[C:10](Cl)[N:11]=[CH:12][C:7]=2[CH:6]=1)=[O:4].C([Si](C)(C)O[CH:27]1[CH2:32][CH2:31][N:30]([C:33]2[CH:34]=[N:35][C:36]([NH2:39])=[CH:37][CH:38]=2)[CH2:29][CH2:28]1)(C)(C)C.CCC[CH2:45][N+:46](CCCC)(CCCC)[CH2:47]CCC.[F-]>C1COCC1>[CH3:1][N:2]([CH3:20])[C:3]([C:5]1[N:14]([CH:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)[C:8]2[N:9]=[C:10]([NH:39][C:36]3[N:35]=[CH:34][C:33]([N:30]4[CH2:29][CH2:28][CH:27]([N:46]([CH3:47])[CH3:45])[CH2:32][CH2:31]4)=[CH:38][CH:37]=3)[N:11]=[CH:12][C:7]=2[CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 2724141Tetrabutylammonium FluorideHCID 583154322-Chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamideHCID 67241098HCID 67241098, compound

Product 1

HCID 44819302HCID 44819302, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following Buchwald Method B, 2-chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethylamide (290 mg, 0.939 mmol) and 4-(tert-butyl-dimethyl-silanyloxy)-3,4,5,6-tetrahydro-2H-[1,3′]bipyridinyl-6′-ylamine (336 mg, 1.09 mmol). Followed by deprotection using 7 mL of TBAF in 28 mL of THF to give 7-cyclopentyl-2-(4-dimethylamino-3,4,5,6-tetrahydro-2H-[1,3]bipyridinyl-6′-ylamino)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethylamide (110 mg, 61%). MS (ESI) m/z 450.3 (M+H)+

Sources & evidence

ORD record
ord-255813d34918453f9810f137ff9b961f
Source dataset
uspto-grants-2014_04
Patent number
US08685980B2

Reaction notes

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