Triethylamine → [3-({5-Nitro-4-[(4-pyrrolidin-1-yl-cyclohexylmethyl)amino]-pyrimidin-2-ylamino}-methyl)-benzyl]-carbamic acid tert-butyl ester

HRID 1819476Notes

Reaction equation

HRID 1819476 reaction equation
[N:1]1([CH:6]2[CH2:11][CH2:10][CH:9](NC)[CH2:8][CH2:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C[CH2:15][N:16](CC)CC.[C:21]([O:25][C:26](=[O:49])[NH:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([CH2:35][NH:36][C:37]2[N:42]=[C:41](SC#N)[C:40]([N+:46]([O-:48])=[O:47])=[CH:39][N:38]=2)[CH:30]=1)([CH3:24])([CH3:23])[CH3:22]>CCO>[C:21]([O:25][C:26](=[O:49])[NH:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([CH2:35][NH:36][C:37]2[N:42]=[C:41]([NH:16][CH2:15][CH:9]3[CH2:8][CH2:7][CH:6]([N:1]4[CH2:2][CH2:3][CH2:4][CH2:5]4)[CH2:11][CH2:10]3)[C:40]([N+:46]([O-:48])=[O:47])=[CH:39][N:38]=2)[CH:30]=1)([CH3:23])([CH3:22])[CH3:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 57457676(4-Pyrrolidin-1-yl-cyclohexyl)-methylamineHCID 57885599{3-[(5-Nitro-4-thiocyanato-pyrimidin-2-ylamino)-methyl]-benzyl}-carbamic acid tert-butyl ester

Product 1

HCID 57885727[3-({5-Nitro-4-[(4-pyrrolidin-1-yl-cyclohexylmethyl)amino]-pyrimidin-2-ylamino}-methyl)-benzyl]-carbamic acid tert-butyl esterYield 135.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (4-pyrrolidin-1-yl-cyclohexyl)-methylamine(32 mg, 0.18 mmol) and Et3N (26 μL, 0.18 mmol) in EtOH (2 mL) was added {3-[(5-nitro-4-thiocyanato-pyrimidin-2-ylamino)-methyl]-benzyl}-carbamic acid tert-butyl ester (74 mg, 0.18 mmol). The reaction mixture was stirred at room temperature overnight before concentrating in vacuo. The residue was purified by chromatography using an ISCO combi-flash cartridge (silica gel, 50:50 to 0:100 DCM/80:18:2 DCM/MeOH/NH4OH) to afford impure [3-({5-nitro-4-[(4-pyrrolidin-1-yl-cyclohexylmethyl)-amino]-pyrimidin-2-ylamino}-methyl)-benzyl]-carbamic acid tert-butyl ester (132 mg), m/z 540 (M+1)+

Workup

  1. concentrationbefore concentrating in vacuo
  2. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-a597d572af364d908dd994b99c5a5f7d
Source dataset
uspto-grants-2009_10
Patent number
US07601714B2

Reaction notes

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