Sodium hydride → [4-(4-{5-[6-(2-Methoxy-ethoxy)-naphthalen-2-yl]-pyrazolo[1,5-c]pyrimidin-7-ylamino}-phenylcarbamoyl)-benzyl]-carbamic acid tert-butyl ester

HRID 19603Notes

Reaction equation

HRID 19603 reaction equation
[C:1]([O:5][C:6](=[O:45])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:44])[NH:16][C:17]2[CH:22]=[CH:21][C:20]([NH:23][C:24]3[N:29]4[N:30]=[CH:31][CH:32]=[C:28]4[CH:27]=[C:26]([C:33]4[CH:42]=[CH:41][C:40]5[C:35](=[CH:36][CH:37]=[C:38]([OH:43])[CH:39]=5)[CH:34]=4)[N:25]=3)=[CH:19][CH:18]=2)=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Br[CH2:49][CH2:50][O:51][CH3:52]>CN(C=O)C>[C:1]([O:5][C:6](=[O:45])[NH:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]([C:15](=[O:44])[NH:16][C:17]2[CH:22]=[CH:21][C:20]([NH:23][C:24]3[N:29]4[N:30]=[CH:31][CH:32]=[C:28]4[CH:27]=[C:26]([C:33]4[CH:42]=[CH:41][C:40]5[C:35](=[CH:36][CH:37]=[C:38]([O:43][CH2:49][CH2:50][O:51][CH3:52])[CH:39]=5)[CH:34]=4)[N:25]=3)=[CH:19][CH:18]=2)=[CH:13][CH:14]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 809722-Bromoethyl methyl etherHCID 136388310HCID 136388310, compound2×

Product 1

HCID 67318656[4-(4-{5-[6-(2-Methoxy-ethoxy)-naphthalen-2-yl]-pyrazolo[1,5-c]pyrimidin-7-ylamino}-phenylcarbamoyl)-benzyl]-carbamic acid tert-butyl esterYield 52%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (4-{4-[5-(6-hydroxy-naphthalen-2-yl)-pyrazolo[1,5-c]pyrimidin-7-ylamino]-phenylcarbamoyl}-benzyl)-carbamic acid tert-butyl ester (compound A3)(120 mg) in DMF (3 ml) are added NaH (8 mg) and 2-bromoethylmethylether (0.019 ml). The mixture is stirred overnight and after extraction the crude product is purified by silica gel flash chromatography. A nearly colorless solid (68 mg) in 52% yield is obtained.

Workup

  1. extractionafter extraction the crude product
  2. customis purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-9ce29407f44e4ea489fb6248848e3344
Source dataset
uspto-grants-2010_06
Patent number
US07745446B2

Reaction notes

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