Sodium triacetoxyborohydride → HCID 178432376, compound

HRID 1851292Notes

Reaction equation

HRID 1851292 reaction equation
[CH3:1][C:2]1[N:24]=[C:5]2[N:6]=[C:7]([C:16]3[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][CH:17]=3)[C:8]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:9][N:4]2[N:3]=1.C[O:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]2[NH:34][N:35]=[C:36]([CH:38]3[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]3)[N:37]=2)=[CH:29][N:28]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl.C1COCC1.O.CC(O[Ti](OC(C)C)(OC(C)C)OC(C)C)C>[CH3:1][C:2]1[N:24]=[C:5]2[N:6]=[C:7]([C:16]3[CH:17]=[CH:18][C:19]([CH2:20][N:41]4[CH2:42][CH2:43][CH:38]([C:36]5[N:37]=[C:33]([C:30]6[CH:31]=[CH:32][C:27]([OH:26])=[N:28][CH:29]=6)[NH:34][N:35]=5)[CH2:39][CH2:40]4)=[CH:22][CH:23]=3)[C:8]([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)=[CH:9][N:4]2[N:3]=1

Participants

8

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 866306814-(2-Methyl-6-phenyl[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)benzaldehydeHCID 178488932HCID 178488932, compound

Product 1

HCID 178432376HCID 178432376, compound

Reagents, catalysts & solvents 4

HCID 178460666HCID 178460666, compoundCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-(2-methyl-6-phenyl-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)benzaldehyde (293 mg, 1 mmol) and 2-methoxy-5-(5-piperidin-4-yl-2H-[1,2,4]triazol-3-yl)-pyridine (0.58 g) in CH2Cl2 (5 mL) and THF (23 mL) was treated with Ti(OiPr)4 (0.82 mL) and stirred overnight at rt. The mixture was treated with NaBH(OAc)3 (395 mg) and stirred for 2 hours at rt. The reaction was diluted with CH2Cl2 and water and filtered through Celite. The phases were separated and the organic phase was washed with brine. The Celite pad was washed with MeOH and the combined organic portions were concentrated in vacuo. Purification was achieved by preparative HPLC to give the title compound.

Workup

  1. stirringstirred for 2 hours at rt
  2. filtrationfiltered through Celite
  3. customThe phases were separated
  4. washthe organic phase was washed with brine
  5. washThe Celite pad was washed with MeOH
  6. concentrationthe combined organic portions were concentrated in vacuo
  7. customPurification

Sources & evidence

ORD record
ord-a3e2b373a2044db0b5e0f6a6596dd02d
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

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