Sodium Bicarbonate → HCID 66599980, compound

HRID 1621369Notes

Reaction equation

HRID 1621369 reaction equation
F[C:2]1[C:7]([C:8]2[N:16]=[CH:15][N:14]=[C:13]3[C:9]=2[N:10]=[CH:11][N:12]3[CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][O:18]2)=[CH:6][CH:5]=[CH:4][N:3]=1.[C:23]([NH:26][C:27]1[CH:32]=[CH:31][C:30]([NH2:33])=[CH:29][N:28]=1)(=[O:25])[CH3:24].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.C([O-])(O)=O.[Na+]>C1COCC1>[O:18]1[CH2:19][CH2:20][CH2:21][CH2:22][CH:17]1[N:12]1[CH:11]=[N:10][C:9]2[C:13]1=[N:14][CH:15]=[N:16][C:8]=2[C:7]1[C:2]([NH:33][C:30]2[CH:31]=[CH:32][C:27]([NH:26][C:23](=[O:25])[CH3:24])=[N:28][CH:29]=2)=[N:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 2733832Lithium HexamethyldisilazideHCID 27352192-Acetamido-5-aminopyridineHCID 44479178HCID 44479178, compound

Product 1

HCID 66599980HCID 66599980, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 6-(2-fluoropyridin-3-yl)-9-(tetrahydro-2H-pyran-2-yl)-9H-purine (300 mg, 1002 μmol) and 2-acetamido-5-aminopyridine (Aldrich, St. Louis, Mo.) (152 mg, 1002 μmol) was suspended in THF (2 mL) and treated with LiHMDS (1.0 M in THF, Aldrich, St. Louis, Mo.) (4009 μl, 4009 μmol). The mixture was stirred for 16 h and then poured into saturated aqueous NaHCO3, extracting with EtOAc. Some dark orange insoluble material was observed. The EtOAc extract was dried (MgSO4), filtered and concentrated to give N-(5-(3-(9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)pyridin-2-ylamino)pyridin-2-yl)acetamide (324 mg, 75% yield) as an orange solid. 1H NMR (CDCl3, 300 MHz) δ 12.35 (s, 1H), 9.73 (dd, 1H), 9.04 (s, 1H), 8.69 (bs, 1H), 8.37 (s, 1H), 8.35 (dd, 1H), 8.21 (bs, 2H), 8.00 (bs, 1H), 6.96 (dd, 1H), 5.89 (dd, 1H), 4.23 (m, 1H), 3.84 (m, 1H), 2.21 (s, 3H), 2.3-17 (m, 8H); m/z (API-ES) 431, (M+H)+.

Workup

  1. extractionextracting with EtOAc
  2. extractionThe EtOAc extract
  3. dry with materialwas dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-59c90a77f55b4e1ab8185c25c4b99b3f
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

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