Iodine → HCID 11719282, compound

HRID 2222079Notes

Reaction equation

HRID 2222079 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[N:11]=[C:10]([NH:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:9]=[C:8]2[C:4]=1[N:5]=[CH:6][N:7]2[CH3:21].C(O)C.C(=O)=O.[Li]CCCC.[I:35]I>CCCCCC.C1COCC1>[I:35][C:6]1[N:7]([CH3:21])[C:8]2[C:4]([N:5]=1)=[C:3]([C:2]([F:1])([F:22])[F:23])[N:11]=[C:10]([NH:12][CH2:13][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[N:9]=2

Participants

7

Reactant 4

HCID 807IodineHCID 11702516HCID 11702516, compound2×HCID 19604758Methanedione--ethanol (1/1)HCID 178418339Butyllithium

Product 1

HCID 11719282HCID 11719282, compoundYield 91.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

6-Trifluoromethyl-9-methyl-2-phenethylaminopurine (compound 10) (0.500 g, 1.56 mmol) was dried in vacuo at 100° C. for 2.5 h. After cooling, dry THF (18 ml) was added at room temperature and the solution was cooled to −72° C. (ethanol/dry ice). After addition of n-BuLi (2.4 ml of a 1.6 M solution in hexane, 3.9 mmol) the colourless solution turned yellow. After 15 minutes I2 (0.633 g, 2.49 mmol) was added and after 5 minutes the reaction was complete (HPLC: Rt,product=4.7). To the red solution silica gel (˜4 g) was added and the suspension was evaporated to dryness. Flash chromatography (1% MeOH in MTBE) and freezedrying afforded the product (0.637 g, 91%) as fluffy white crystals, mp 139-142° C. 1H-NMR (400 MHz, CDCl3), δ [ppm]: 7.33-7.21 (m, 5H, Har), 5.96 (br s, 1H, NH), 3.93 (br m, 2H, NHCH2), 3.77 (s, 3H, CH3), 2.98 (t, J=7.1 Hz, 2H, CH2). 19F-NMR (500 MHz, CDCl3), δ [ppm]: −70.12 (6-CF3).

Workup

  1. temperatureAfter cooling
  2. additionTo the red solution silica gel (˜4 g) was added
  3. customthe suspension was evaporated to dryness
  4. dry with materialFlash chromatography (1% MeOH in MTBE) and freezedrying

Sources & evidence

ORD record
ord-d41f2782226d494980025306eceae2a6
Source dataset
uspto-grants-2008_05
Patent number
US07371737B2

Reaction notes

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