Diethylamine → 2-[4-(4-chloro-7-(3-tetrahydrofuryl)-7H-pyrrolo[2,3-d)pyrimidin-5-yl)phenoxy]-N,N-diethylbenzylamine

HRID 51484Notes

Reaction equation

HRID 51484 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl:15][C:16]1[C:17]2[C:24]([C:25]3[CH:39]=[CH:38][C:28]([O:29][C:30]4[CH:37]=[CH:36][CH:35]=[CH:34][C:31]=4[CH:32]=O)=[CH:27][CH:26]=3)=[CH:23][N:22]([CH:40]3[CH2:44][CH2:43][O:42][CH2:41]3)[C:18]=2[N:19]=[CH:20][N:21]=1.[CH2:45]([NH:47][CH2:48][CH3:49])[CH3:46]>ClCCCl>[Cl:15][C:16]1[C:17]2[C:24]([C:25]3[CH:26]=[CH:27][C:28]([O:29][C:30]4[CH:37]=[CH:36][CH:35]=[CH:34][C:31]=4[CH2:32][N:47]([CH2:48][CH3:49])[CH2:45][CH3:46])=[CH:38][CH:39]=3)=[CH:23][N:22]([CH:40]3[CH2:44][CH2:43][O:42][CH2:41]3)[C:18]=2[N:19]=[CH:20][N:21]=1

Participants

5

Reactant 3

HCID 8021DiethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 86589002(4-(4-chloro-7-(3-tetrahydrofuryl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)phenoxy]benzaldehyde

Product 1

HCID 865890012-[4-(4-chloro-7-(3-tetrahydrofuryl)-7H-pyrrolo[2,3-d)pyrimidin-5-yl)phenoxy]-N,N-diethylbenzylamine

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Sodium triacetoxyborohydride (264 mg) was added to a mixture of 2-[(4-(4-chloro-7-(3-tetrahydrofuryl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)phenoxy]benzaldehyde (330 mg) and diethylamine (121 mg) in 1,2-dichloroethane in a vial (5 ml) and the vial septum sealed. The mixture was stirred at ambient temperature for 20 hours then quenched with saturated aqueous sodium bicarbonate solution (5 ml). The mixture was extracted with ethyl acetate to give 2-[4-(4-chloro-7-(3-tetrahydrofuryl)-7H-pyrrolo[2,3-d)pyrimidin-5-yl)phenoxy]-N,N-diethylbenzylamine.

Workup

  1. customthe vial septum sealed
  2. customthen quenched with saturated aqueous sodium bicarbonate solution (5 ml)
  3. extractionThe mixture was extracted with ethyl acetate

Sources & evidence

ORD record
ord-1fa94fc079394ebda30b643864d0c238
Source dataset
uspto-grants-2004_03
Patent number
US06713474B2

Reaction notes

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