Acetone → HCID 11306778, compound

HRID 1785439Notes

Reaction equation

HRID 1785439 reaction equation
[NH2:1][CH2:2][CH2:3][CH:4]1[CH2:20][N:8]2[C:9](=[O:19])[CH:10]=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:12]=[C:7]2[N:6]([C:21]2[CH:26]=[CH:25][N:24]=[C:23]([NH:27][CH2:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[N:22]=2)[CH2:5]1.[CH3:36][C:37]([CH3:39])=O.ClCCl.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO>[CH:37]([NH:1][CH2:2][CH2:3][CH:4]1[CH2:20][N:8]2[C:9](=[O:19])[CH:10]=[C:11]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:12]=[C:7]2[N:6]([C:21]2[CH:26]=[CH:25][N:24]=[C:23]([NH:27][CH2:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[N:22]=2)[CH2:5]1)([CH3:39])[CH3:36]

Participants

6

Reactant 4

HCID 180AcetoneHCID 6344DichloromethaneHCID 5049666Sodium triacetoxyborohydrideHCID 57593142HCID 57593142, compound

Product 1

HCID 11306778HCID 11306778, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 7-(2-Amino-ethyl)-9-(2-phenethylamino-pyrimidin-4-yl)-2-phenyl-6,7,8,9-tetrahydro-pyrimido[1,2-a]pyrimidin-4-one (70 mg, 0.15 mmol), acetone (0.02 mL), dichloromethane (0.5 mL) and methanol (0.5 mL) was added sodium triacetoxyborohydride (38 mg, 0.18 mmol) Reaction stirred for 2 h at room temperature. Solvents removed under vacuum. Residue partitioned between dichloromethane and 5% sodium bicarbonate. Organics purified on silica to afford a white solid. M+1=510. 1NMR (CDCl3) d (6H, 1.17 ppm), m (2H, 1.68 ppm), m (1H, 2.32 ppm), m (3H, 2.78 ppm), t (2H, 2.94 ppm), m (1H, 3.55 ppm), dd (2H, 3.70 ppm), d (1H, 4.40 ppm), dd (1H, 4.53 ppm), m (1H, 5.10 ppm), s (1H, 6.60 ppm), m (3H, 7.24 ppm), m (2H, 7.32 ppm), m (3H, 7.44 ppm), m (2H, 7.90 ppm) d (1H, 8.18 ppm).

Workup

  1. customSolvents removed under vacuum
  2. customResidue partitioned between dichloromethane and 5% sodium bicarbonate
  3. customOrganics purified on silica
  4. customto afford a white solid

Sources & evidence

ORD record
ord-13259bf123d54673ac4b4e67de5cd963
Source dataset
uspto-grants-2009_03
Patent number
US07504403B2

Reaction notes

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