Acetone → HCID 57833241, compound

HRID 729919Notes

Reaction equation

HRID 729919 reaction equation
[CH3:1][C:2]([CH3:4])=O.[NH2:5][CH2:6][C:7]1[CH:12]=[C:11]([O:13][C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21]3[CH:26]=[C:25]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[N:24]=[C:23]([NH2:33])[N:22]=3)=[CH:16][CH:15]=2)[CH:10]=[CH:9][N:8]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.C[O-].[Ti+4].C[O-].C[O-].C[O-]>[CH:2]([NH:5][CH2:6][C:7]1[CH:12]=[C:11]([O:13][C:14]2[CH:15]=[CH:16][C:17]([NH:20][C:21]3[CH:26]=[C:25]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[N:24]=[C:23]([NH2:33])[N:22]=3)=[CH:18][CH:19]=2)[CH:10]=[CH:9][N:8]=1)([CH3:4])[CH3:1]

Participants

6

Reactant 3

HCID 180AcetoneHCID 5049666Sodium triacetoxyborohydrideHCID 57833404HCID 57833404, compound

Product 1

HCID 57833241HCID 57833241, compoundYield 42.2%

Reagents, catalysts & solvents 2

HCID 164767Titanium tetra(methanolate)CatalystHCID 6344DichloromethaneSolvent

Procedure

Acetone (11.51 mg, 0.20 mmol), N4-(4-{[2-(aminomethyl)pyridin-4-yl]oxy}phenyl)-6-phenylpyrimidine-2,4-diamine (80 mg, 0.21 mmol, Example 39) and titanium (IV) methoxide (68.2 mg, 0.40 mmol) were suspended in CH2Cl2 (5 mL) and stirred at rt for 24 h. Sodium triacetoxyborohydride (105 mg, 0.50 mmol) was added into the reaction mixture and the mixture was stirred at rt for another 24 h. The mixture was filtered through a Celite® pad and washed with CH2Cl2. A small amount of Celite® was added to the filtrate and 5 mL of water was added to quench the reaction. After it was stirred for 20 min, the CH2Cl2 was removed in vacuo. The residue was taken up in ethyl acetate and washed with 1N NaOH (2×) and water (3×). The organic layer was concentrated and purified by Prep-TLC (MeOH) to give 36 mg (42.2%) of the title product as a white solid. 1H NMR (CD3OD) δ 8.35 (d, 1H), 7.82 (d, 2H), 7.00 (d, 2H), 7.44 (m, 3H), 7.08 (m, 2H), 7.01 (s, 1H), 6.82 (m, 1H), 6.46 (s, 1H), 3.81 (s, 2H), 2.80 (m, 1H), 1.10 (d, 6H); MS ES 427 (M+H)+, calcd 427, RT=2.59 min; TLC (MeOH)Rf=0.38.

Workup

  1. stirringthe mixture was stirred at rt for another 24 h
  2. filtrationThe mixture was filtered through a Celite® pad
  3. washwashed with CH2Cl2
  4. additionA small amount of Celite® was added to the filtrate and 5 mL of water
  5. additionwas added
  6. customto quench
  7. customthe reaction
  8. stirringAfter it was stirred for 20 min
  9. customthe CH2Cl2 was removed in vacuo
  10. washwashed with 1N NaOH (2×) and water (3×)
  11. concentrationThe organic layer was concentrated
  12. custompurified by Prep-TLC (MeOH)

Sources & evidence

ORD record
ord-84be1e923824489dab17f114323f0f99
Source dataset
uspto-grants-2009_09
Patent number
US07582645B2

Reaction notes

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