Chloride → HCID 18362931, compound

HRID 322829Notes

Reaction equation

HRID 322829 reaction equation
I[C:2]1[N:3]([CH2:18][C:19]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:22]=[CH:21][CH:20]=2)[CH:4]=[C:5]2[C:10]=1[C:9](=[O:11])[N:8]([CH3:12])[C:7](=[O:13])[N:6]2[CH2:14][CH:15]([CH3:17])[CH3:16].[CH2:29]([OH:34])[CH2:30][CH2:31][C:32]#[CH:33].[Cl-].C(#N)C>C(N(CC)CC)C.[Cu]I>[OH:34][CH2:29][CH2:30][CH2:31][C:32]#[C:33][C:2]1[N:3]([CH2:18][C:19]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:22]=[CH:21][CH:20]=2)[CH:4]=[C:5]2[C:10]=1[C:9](=[O:11])[N:8]([CH3:12])[C:7](=[O:13])[N:6]2[CH2:14][CH:15]([CH3:16])[CH3:17]

Participants

7

Reactant 4

HCID 312ChlorideHCID 6342AcetonitrileHCID 793464-Pentyn-1-olHCID 18362930HCID 18362930, compound

Product 1

HCID 18362931HCID 18362931, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8471TriethylamineSolvent

Procedure

5-Iodo-3-methyl-1-(2-methylpropyl)-6-(1-naphthalenylmethyl)-1H-pyrrolo-[3,4-d]pyrimidine-2,4(3H,6H)-dione (100 mg), 4-pentyn-1-ol (0.080 ml), bis-triphenylphosphinepalladium (II) chloride (3 mg) and copper (I) iodide (1 mg) were dissolved in triethylamine (3 ml) and acetonitrile (1 ml) and heated to 90° C. in a sealed pressure tube for 3 hours. The reaction mixture was allowed to cool to room temperature and was then evaporated to leave a residue which was recrystallised from ethyl acetate. The resultant brown solid was chromatographed, eluting with ethyl acetate to give a white solid which was triturated with ethyl acetate to give the title compound (45 mg). Melting point: 176-177° C. MS (APCI+ve) 444 (M+H)+ 1H NMR (CDCl3) δ 0.84 (d, 6H), 1.82 (m, 2H), 2.08 (m, 1H), 2.36 (t, 1H), 2.65 (t, 2H), 3.40 (s, 3H), 3.50 (d, 2H), 3.77 (q, 2H), 5.67 (s, 2H), 6.10 (s, 1H), 7.08 (d, 1H), 7.47 (dd, 1H), 7.55 (m, 2H), 7.86-7.94 (m, 3H)

Workup

  1. customwas then evaporated
  2. customto leave a residue which
  3. customwas recrystallised from ethyl acetate
  4. customThe resultant brown solid was chromatographed
  5. washeluting with ethyl acetate
  6. customto give a white solid which
  7. customwas triturated with ethyl acetate

Sources & evidence

ORD record
ord-fce9d5e2d59a4ddfa8d013e3c8db0aaa
Source dataset
uspto-grants-2001_04
Patent number
US06211368B1

Reaction notes

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