Diisopropylethylamine → 3-(4-((1R,4R)-4-(tert-butyldiphenylsilyloxy)-1,2,3,4-tetrahydronaphthalen-1-ylamino)-5-nitropyrimidin-2-yl)-3H-benzo[d]imidazole-5-carbonitrile

HRID 1363244Notes

Reaction equation

HRID 1363244 reaction equation
[Si:1]([O:18][C@H:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C@H:22]([NH2:29])[CH2:21][CH2:20]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[C:39]([C:41]1[CH:42]=[CH:43][C:44]2[N:48]=[CH:47][N:46]([C:49]3[N:54]=[C:53](SC#N)[C:52]([N+:58]([O-:60])=[O:59])=[CH:51][N:50]=3)[C:45]=2[CH:61]=1)#[N:40]>C1COCC1>[Si:1]([O:18][C@H:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C@H:22]([NH:29][C:51]2[C:52]([N+:58]([O-:60])=[O:59])=[CH:53][N:54]=[C:49]([N:46]3[C:45]4[CH:61]=[C:41]([C:39]#[N:40])[CH:42]=[CH:43][C:44]=4[N:48]=[CH:47]3)[N:50]=2)[CH2:21][CH2:20]1)([C:14]([CH3:16])([CH3:17])[CH3:15])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 533895902-(6-Cyano-1H-benzimidazol-1-yl)-5-nitropyrimidin-4-yl thiocyanateHCID 59704938(1R,4R)-4-(tert-Butyldiphenylsilyloxy)-1,2,3,4-tetrahydronaphthalen-1-amine

Product 1

HCID 669708173-(4-((1R,4R)-4-(tert-butyldiphenylsilyloxy)-1,2,3,4-tetrahydronaphthalen-1-ylamino)-5-nitropyrimidin-2-yl)-3H-benzo[d]imidazole-5-carbonitrileYield 78.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of (1R,4R)-4-(tert-butyldiphenylsilyloxy)-1,2,3,4-tetrahydronaphthalen-1-amine (4.0 g) and DIEA (5.3 mL) in anhydrous THF (20 mL) were added via syringe over 1 min to 6-cyano-1-(5-nitro-4-thiocyanatopyrimidin-2-yl)-1H-benzo[d]imidazole (3.43 g, 10.601 mM) in THF at 0° C. The resulting solution was allowed to warm slowly to RT overnight, then partitioned between water and DCM. Column purification (1% MeOH/DCM) gave the titled product (5.21 g), MH+=666.

Workup

  1. custompartitioned between water and DCM
  2. customColumn purification (1% MeOH/DCM)

Sources & evidence

ORD record
ord-0d8df0aaba404e1dbf5f6432d454fc77
Source dataset
uspto-grants-2011_02
Patent number
US07884109B2

Reaction notes

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