* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Reference：
[1] Journal of the American Chemical Society, 2010, vol. 132, # 12, p. 4455 - 4465
[2] Patent: WO2006/114409, 2006, A1, . Location in patent: Page/Page column 20-21
N-[4-(2-amino-4-chloropyrimidin-6-yloxymethyl)-benzyl]-6-biotinylamino-hexanoylcarboxamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With triethylamine; In N,N-dimethyl-formamide; at 20.0℃; for 24.0h;
Example 14: N-[4-(2-Amino-4-chloropyrinnidin-6-yloxynnethyl)-benzyl1-6-biotinylannino- hexanoylcarboxamide (23)6-(4-Aminomethyl-benzyloxy)-2-amino-4-chloropyrimidine (16, 3.5 mg, 0.015 mmol) and N- (+)-biotinyl-aminocaproic acid succinimidyl ester (3.5 mg, 0.007 mmol) are dissolved in 300 mul_ DMF with 4 mul_ TEA and left at room temperature for 24 h. The product is purified by reversed phase MPLC on a C18 column using a linear gradient water: acetonitrile (from 95:5 to 20:80 in 20 min, 0.08 % TFA). MS (ESI) m/z 604.2 [M+H]+.
2-(3,6-bis(dimethylamino)xanthylium-9-yl)-4-(((2,5-dioxopyrrolidin-1-yl)oxy)carbonyl)benzoate[ No CAS ]
5-carboxytetramethylrhodamine succinimidyl ester[ No CAS ]
N-[4-(2-amino-4-chloropyrimidin-6-yloxymethyl)-benzyl]-tetramethylrhodamine-5-carboxamide[ No CAS ]
N-[4-(2-amino-4-chloropyrimidin-6-yloxymethyl)-benzyl]-tetramethylrhodamine-6-carboxamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With triethylamine; In N,N-dimethyl-formamide; at 20.0℃; for 24.0h;
Examplel O: N-[4-(2-Amino-4-chloropyrimidin-6-yloxymethyl)-benzyl1-tetramethylrhodamine- 6-carboxamide (17) and N-[4-(2-amino-4-chloropyrimidin-6-yloxymethyl)-benzyl1- tetramethylrhodamine-5-carboxamide (18)6-(4-Aminomethyl-benzyloxy)-2-amino-4-chloropyrimidine (16, 8 mg, 0.03 mmol) and 5(6)- carboxytetramethylrhodamine succinimidyl ester (7.47 mg, 0.014 mmol) are dissolved in 850 mul_ DMF with 20 mul_ TEA and left at room temperature for 24 h. The product is purified and the 5 and 6 isomers separated by reversed phase MPLC on a C18 column using a linear gradient wateracetonitrile (from 95:5 to 20:80 in 20 min, 0.08% TFA). MS (ESI) m/z 714.7 [M- Cl]+.
Example 9: 6-(4-Aminomethyl-benzyloxy)-2-amino-4-chloropyrimidine (16)65 mg (0.18 mmol) N-[4-(2-amino-4-chloropyrimidin-6-yloxymethyl)-benzyl]-2,2,2-trifluoro- acetamide (15) is dissolved in 1 mL methanol and treated with 2 mL methylamine (33% in ethanol). The reaction mixture is stirred at room temperature over night and all volatiles are EPO <DP n="22"/>removed in vacuo. The product is used without further purification in the next step. ESI-MS m/z 265.3 [M+H]+.
5-carboxy-2-(7-(dimethylamino)-3-(dimethyliminio)-5,5-dimethyl-3,5-dihydrodibenzo[b,e]silin-10-yl)benzoate[ No CAS ]
SiR650-5CP[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
80%
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dimethyl sulfoxide; at 20.0℃;
General procedure: 06-(4-Aminomethyl)benzylguanine (BG-NH2) and 4-(4-aminomethyl)benzyloxy-6- chloropyrimidin-2-amine (CP-NH2) were prepared according to the previously reported procedures (Keppler et al., Methods 2004, 32, 437; Srikun et al., C.J. J.Am. Chem.Soc. 2010, 132, 4455), respectively. SiR dyes (5.0 mg, 1 eq.), BG-NH2 (6.5 mg 2.4 eq.) or CP-NH2 (6.4 mg, 2.4 eq.), PyBOP (12.0 mg, 2.4 eq.) were dissolved in dry DMSO (500 muIota) in the presence of DIEA (10 muIota), and the solution was stirred at room temperature for 1 -3 hr. The reaction mixture was purified by HPLC to obtain the desired BG- or CP- SiR conjugates
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dimethyl sulfoxide; at 20.0℃;
General procedure: 06-(4-Aminomethyl)benzylguanine (BG-NH2) and 4-(4-aminomethyl)benzyloxy-6- chloropyrimidin-2-amine (CP-NH2) were prepared according to the previously reported procedures (Keppler et al., Methods 2004, 32, 437; Srikun et al., C.J. J.Am. Chem.Soc. 2010, 132, 4455), respectively. SiR dyes (5.0 mg, 1 eq.), BG-NH2 (6.5 mg 2.4 eq.) or CP-NH2 (6.4 mg, 2.4 eq.), PyBOP (12.0 mg, 2.4 eq.) were dissolved in dry DMSO (500 muIota) in the presence of DIEA (10 muIota), and the solution was stirred at room temperature for 1 -3 hr. The reaction mixture was purified by HPLC to obtain the desired BG- or CP- SiR conjugates
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dimethyl sulfoxide; at 20.0℃;
General procedure: 06-(4-Aminomethyl)benzylguanine (BG-NH2) and 4-(4-aminomethyl)benzyloxy-6- chloropyrimidin-2-amine (CP-NH2) were prepared according to the previously reported procedures (Keppler et al., Methods 2004, 32, 437; Srikun et al., C.J. J.Am. Chem.Soc. 2010, 132, 4455), respectively. SiR dyes (5.0 mg, 1 eq.), BG-NH2 (6.5 mg 2.4 eq.) or CP-NH2 (6.4 mg, 2.4 eq.), PyBOP (12.0 mg, 2.4 eq.) were dissolved in dry DMSO (500 muIota) in the presence of DIEA (10 muIota), and the solution was stirred at room temperature for 1 -3 hr. The reaction mixture was purified by HPLC to obtain the desired BG- or CP- SiR conjugates
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dimethyl sulfoxide; at 20.0℃;
General procedure: 06-(4-Aminomethyl)benzylguanine (BG-NH2) and 4-(4-aminomethyl)benzyloxy-6- chloropyrimidin-2-amine (CP-NH2) were prepared according to the previously reported procedures (Keppler et al., Methods 2004, 32, 437; Srikun et al., C.J. J.Am. Chem.Soc. 2010, 132, 4455), respectively. SiR dyes (5.0 mg, 1 eq.), BG-NH2 (6.5 mg 2.4 eq.) or CP-NH2 (6.4 mg, 2.4 eq.), PyBOP (12.0 mg, 2.4 eq.) were dissolved in dry DMSO (500 muIota) in the presence of DIEA (10 muIota), and the solution was stirred at room temperature for 1 -3 hr. The reaction mixture was purified by HPLC to obtain the desired BG- or CP- SiR conjugates
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
For Research Only
110K+ Compounds
Competitive Price
1-2 Day Shipping
