Chloroform → HCID 178506017, compound

HRID 2047667Notes

Reaction equation

HRID 2047667 reaction equation
Cl[C:2]1[N:10]=[C:9]([F:11])[N:8]=[C:7]2[C:3]=1[NH:4][CH:5]=[N:6]2.C(N(C(C)C)CC)(C)C.[NH2:21][CH2:22][C:23]1[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=1.C(Cl)(Cl)Cl>CCCCO.CO>[F:11][C:9]1[N:8]=[C:7]2[C:3]([N:4]=[CH:5][NH:6]2)=[C:2]([NH:21][CH2:22][C:23]2[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=2)[N:10]=1

Participants

7

Reactant 4

HCID 6212ChloroformHCID 773174-PyridinemethanamineHCID 81531DiisopropylethylamineHCID 52879146-Chloro-2-fluoropurine

Product 1

HCID 178506017HCID 178506017, compound

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 887MethanolSolvent

Procedure

To a stirred solution of 6-chloro-2-fluoropurine (1 g, 5.8 mmol) in n-BuOH (50 mL) under an argon atmosphere at 0° C., was added diisopropylethylamine (3 ml, 17.4 mmol) followed by 4-(aminomethyl)pyridine (0.9 ml, 1.5 eq, 8.7 mmol). The reaction mixture was stirred at this temperature for 1 h and then allowed to return to room temperature and stirred for 4 h, when TLC(CHCl3:MeOH; 90:10) indicated that the reaction had gone to completion. The solvent was evaporated in vacuo and the residue was purified by gradient flash column chromatography on silica gel, eluted with CHCl3:MeOH (100:0→90:10), to afford the product as a white solid; Yield: 0.85 g (60%). mp 200-202° C. 1H-NMR (d6-DMSO, 250 MHz): δ 4.67 (2 H, d, J 5, —HNCH2-Pyr), 7.34-7.28 (2 H, m, Pyr-H), 8.48-8.42 (2 H, m, Pyr-H), 8.54 (1 H, s, —N═CH—NH—), 8.84 (1 H, s, br, —HNCH2-Pyr), 13.13 (1 H, s, b, —N═CH—NH—); m/z 245 ([M+H]+

Workup

  1. customto return to room temperature
  2. stirringstirred for 4 h
  3. customThe solvent was evaporated in vacuo
  4. customthe residue was purified by gradient flash column chromatography on silica gel
  5. washeluted with CHCl3:MeOH (100:0→90:10)

Sources & evidence

ORD record
ord-ff4bc937ce314995a936ec6c29414a2b
Source dataset
uspto-grants-2013_11
Patent number
US08592581B2

Reaction notes

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