Aminoacetonitrile → ethyl 4-(3-(3-(cyanomethyl)ureido)phenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate

HRID 882133Notes

Reaction equation

HRID 882133 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9]3[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:15][N:14]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[C:10]=3[N:11]=[CH:12][N:13]=2)[CH:5]=[CH:6][CH:7]=1.CCN(C(C)C)C(C)C.[CH:39]1[N:43]=C[N:41]([C:44](N2C=NC=C2)=[O:45])[CH:40]=1.NCC#N>C(Cl)Cl>[C:39]([CH2:40][NH:41][C:44](=[O:45])[NH:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9]3[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:15][N:14]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:28])([CH3:27])[CH3:29])[C:10]=3[N:11]=[CH:12][N:13]=2)[CH:5]=[CH:6][CH:7]=1)#[N:43]

Participants

6

Reactant 4

HCID 10901AminoacetonitrileHCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 89630036ethyl 4-(3-aminophenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate

Product 1

HCID 89629988ethyl 4-(3-(3-(cyanomethyl)ureido)phenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of ethyl 4-(3-aminophenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate (103 mg, 0.250 mmol), DIPEA (0.131 mL, 0.749 mmol) in DCM (1 mL) was added CDI (81 mg, 0.50 mmol). The reaction mixture was stirred at room temperature overnight. At that point aminoacetonitrile (70.0 mg, 1.25 mmol) was added and the reaction mixture was stirred at room temperature for 5 hours. The resulting mixture was concentrated and purified by chromatography on silica eluting with 0-100% ethyl acetate/hexanes to give ethyl 4-(3-(3-(cyanomethyl)ureido)phenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate as a pale yellow solid. LRMS (ESI) calc'd for C24H31N6O4Si [M+H]+: 495, found 495.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 5 hours
  2. concentrationThe resulting mixture was concentrated
  3. custompurified by chromatography on silica eluting with 0-100% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-2f32fe8e70274ff699fe4b18a815e560
Source dataset
uspto-grants-2015_03
Patent number
US08993756B2

Reaction notes

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