Methanol → HCID 68436311, compound

HRID 2354459Notes

Reaction equation

HRID 2354459 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[N:5]=[C:4]2[N:9]([C@@H:13]3[O:18][C@H:17]([CH2:19][OH:20])[C@@H:15]([OH:16])[CH2:14]3)[N:10]=[C:11](I)[C:3]=12.C(N(CC)CC)C.[CH2:28]([O:31][CH3:32])[C:29]#C.CO>CN(C=O)C.C(OCC)(=O)C.[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[N:5]=[C:4]2[N:9]([CH:13]3[O:18][CH:17]([CH2:19][OH:20])[CH:15]([OH:16])[CH2:14]3)[N:10]=[C:11]([C:29]#[C:28][O:31][CH3:32])[C:3]=12

Participants

9

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 693933-MethoxypropyneHCID 15539884HCID 15539884, compound

Product 1

HCID 68436311HCID 68436311, compound

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 4,6-diamino-1-(2-deoxy-β-D-erythro-pentofuranosyl)-3-iodo-1H-pyrazolo[3,4-d]pyrimidine (4.2 g, 10.71 mmol), CuI (211 mg, 1.10 mmol), Pd(PPh3)4 (635 mg, 0.553 mmol), and triethylamine (2.2 mL) in 20 mL of anhydrous DMF was added methyl propargyl ether (1.82 mL). The mixture was stirred under argon for 16 h. and then evaporated to dryness. The residue was crystallized from methanol: 3.20 g (89%) yield; TLC (30% methanol in ethyl acetate), Rf=0.63; 1H NMR (DMSO-d6) δ 7.44 (2H, br d, amino), 6.32 (1H, t, J=6.6 Hz, 1′-H), 6.33 (2H, br s, amino), 5.20 (1H, d, J=4.1 Hz, 3′-OH), 4.75 (1H, br t, 5′-OH), 4.40 (2H, s, methylene), 4.36 (1H, m, 3′-H), 3.76 (1H, m, 4′-H), 3.47 & 3.32 (2H, 2×m, 5′-Hs), 3.32 (3H, s, methoxy), 2.68 & 2.14 (2H, 2×m, 2′-Hs).

Workup

  1. customevaporated to dryness
  2. customThe residue was crystallized from methanol
  3. custom3.20 g (89%) yield

Sources & evidence

ORD record
ord-feca6578a8b743298352f854f72d83c6
Source dataset
uspto-grants-2010_07
Patent number
US07751982B2

Reaction notes

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