Methanol → HCID 22273524, compound

HRID 1064312Notes

Reaction equation

HRID 1064312 reaction equation
C[C:2](C)([O-:4])C.[Na+].[CH3:7][N:8]1[C:12]([C:13]2[CH:18]=[CH:17][N:16]=[C:15]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([S:26](=[O:38])(=[O:37])[NH:27][CH2:28][CH2:29]CN4CCCC4=O)=[CH:22][CH:21]=3)[N:14]=2)=[CH:11][N:10]=[C:9]1[CH3:39].COCCNS(C1C=CC(I)=CC=1)(=O)=O.CO>O1CCOCC1.[Pd].[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:7][N:8]1[C:12]([C:13]2[CH:18]=[CH:17][N:16]=[C:15]([NH:19][C:20]3[CH:21]=[CH:22][C:23]([S:26](=[O:37])(=[O:38])[NH:27][CH2:28][CH2:29][O:4][CH3:2])=[CH:24][CH:25]=3)[N:14]=2)=[CH:11][N:10]=[C:9]1[CH3:39]

Participants

8

Reactant 4

HCID 887MethanolHCID 1587718HCID 1587718, compoundHCID 22273470HCID 22273470, compoundHCID 23676156Sodium t-butoxide

Product 1

HCID 22273524HCID 22273524, compoundYield 84%

Reagents, catalysts & solvents 3

HCID 634876Binap, (A+-)-CatalystHCID 9832798Tris(dibenzylideneacetone) dipalladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

Sodium t-butoxide (1.04 g, 10.8 mmol) was added to a degassed solution of 2-amino-4-(1,2-dimethylimidazol-5-yl)pyrimidine (Method 26; 567 mg, 3 mmol), N-(2-methoxyethyl)-4-iodobenzenesulphonamide (Method 40; 1.54 g, 4.5 mmol), tris(dibenzylideneacetone) dipalladium (0) (72 mg, 0.15 mmol) and 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (102 mg, 0.15 mmol) in dioxane (36 ml) and the mixture heated at 80° C. overnight. The reaction was cooled to room temperature and MeOH (5 ml) was added and the mixture poured onto an Isolute SCX-2 column, eluted first with MeOH (10×30 ml) and the product was then eluted with 2% methanolic ammonia (10×30 ml). The solvent was removed by evaporation and the residue was dissolved in EtOAc (100 ml), washed with water (3×100 ml) and then brine (100 ml), dried and the solvent removed by evaporation to give the title compound (1.01 g, 84%) as a foam. NMR 2.40 (s, 3H), 3.07 (q, 2H), 3.20 (s, 3H), 3.38 (t, 2H), 3.86 (s, 3H), 5.00 (t, 1H), 6.95 (d, 1H), 7.47 (s, 2H), 7.71 (m, 4H), 8.36 (d, 1H); m/z 403.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. additionthe mixture poured onto an Isolute SCX-2 column
  3. washeluted first with MeOH (10×30 ml)
  4. washthe product was then eluted with 2% methanolic ammonia (10×30 ml)
  5. customThe solvent was removed by evaporation
  6. dissolutionthe residue was dissolved in EtOAc (100 ml)
  7. washwashed with water (3×100 ml)
  8. dry with materialbrine (100 ml), dried
  9. customthe solvent removed by evaporation

Sources & evidence

ORD record
ord-5a4ae9f13ff3467fa94f39d16f243af1
Source dataset
uspto-grants-2005_11
Patent number
US06969714B2

Reaction notes

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