Trimethylsilyl iodide → HCID 25155122, compound

HRID 1688139Notes

Reaction equation

HRID 1688139 reaction equation
I[Si](C)(C)C.C(OC([N:16]1[CH2:22][C:21]2[CH:23]=[CH:24][C:25]([NH:27][C:28]3[N:33]=[C:32]([NH:34][C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=4[C:41](=[O:44])[NH:42][CH3:43])[C:31]([Cl:45])=[CH:30][N:29]=3)=[CH:26][C:20]=2[NH:19][C:18](=[O:46])[CH2:17]1)=O)C1C=CC=CC=1>C(Cl)Cl>[Cl:45][C:31]1[C:32]([NH:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=2[C:41]([NH:42][CH3:43])=[O:44])=[N:33][C:28]([NH:27][C:25]2[CH:24]=[CH:23][C:21]3[CH2:22][NH:16][CH2:17][C:18](=[O:46])[NH:19][C:20]=3[CH:26]=2)=[N:29][CH:30]=1

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 67264476HCID 67264476, compound

Product 1

HCID 25155122HCID 25155122, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At 0° C., iodotrimethylsilane (12.3 mg, 0.06 mmol) was added slowly to a solution of 8-[5-chloro-4-(2-methylcarbamoyl-phenylamino)-pyrimidin-2-ylamino]-2-oxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepine-4-carboxylic acid benzyl ester (25 mg, 0.04 mmol) in methylene chloride (5 mL). The mixture solution was warmed to room temperature and stirred for 1 hour. The mixture was quenched with a few drops of methanol, stirred for 10 minutes and concentrated. The residue was treated with 1N HCl (0.5 mL), and then made basic (pH 10) with potassium carbonate. The mixture was extracted with methylene chloride and chloroform, and then dried over sodium sulfate. Chromatography of the crude solid with preparative TLC using methylene chloride and methanol (25:1) gave 6.3 mg of 2-[5-chloro-2-(2-oxo-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-8-ylamino)-pyrimidin-4-ylamino]-N-methyl-benzamide (33%): 1H NMR (300 MHz, CDCl3) δ 8.45 (d, 1H), 8.05 (s, 1H), 7.6 (q, 2H), 7.43 (t, 2H), 7.3 (dd, 1H), 7.13 (d, 2H), 4.0 (s, 2H), 3.43 (s, 2H), 2.92 (s, 3H); MS (m/e): 438.3 (M+1).

Workup

  1. customThe mixture was quenched with a few drops of methanol
  2. stirringstirred for 10 minutes
  3. concentrationconcentrated
  4. additionThe residue was treated with 1N HCl (0.5 mL)
  5. extractionThe mixture was extracted with methylene chloride and chloroform
  6. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-cd67ed754e7744e99ebd5c8f7b0f1f34
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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