Sodium triacetoxyborohydride → 2-[1-(2-Chloro-4-morpholin-4-ylfuro[3,2-d]pyrimidin-6-ylmethyl)piperidin-4-yl]propan-2-ol

HRID 1922859Notes

Reaction equation

HRID 1922859 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[C:5]2[O:10][C:9]([CH:11]=O)=[CH:8][C:6]=2[N:7]=1.[NH:19]1[CH2:24][CH2:23][CH:22]([C:25]([OH:28])([CH3:27])[CH3:26])[CH2:21][CH2:20]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[Cl:1][C:2]1[N:3]=[C:4]([N:13]2[CH2:14][CH2:15][O:16][CH2:17][CH2:18]2)[C:5]2[O:10][C:9]([CH2:11][N:19]3[CH2:24][CH2:23][CH:22]([C:25]([OH:28])([CH3:27])[CH3:26])[CH2:21][CH2:20]3)=[CH:8][C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 52003212-(4-Piperidyl)-2-propanolHCID 568337422-Chloro-4-morpholinofuro[3,2-d]pyrimidine-6-carbaldehyde

Product 1

HCID 596060512-[1-(2-Chloro-4-morpholin-4-ylfuro[3,2-d]pyrimidin-6-ylmethyl)piperidin-4-yl]propan-2-olYield 96.1%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of 2-chloro-4-morpholin-4-ylfuro[3,2-d]pyrimidine-6-carbaldehyde (78 mg, 0.29 mmol) and 2-piperidin-4-ylpropan-2-ol (50 mg, 0.35 mmol) in DCE (3 mL) was stirred at ambient temperature for 45 min. Sodium triacetoxyborohydride (93 mg, 0.44 mmol) was added and the mixture stirred for 2 h, then loaded onto an Isolute® SCX-2 cartridge (10 g). The cartridge was then washed with methanol and the desired product was subsequently eluted using 2 M NH3 in MeOH. The product was collected and concentrated in vacuo. The resultant residue was purified by flash chromatography (Si—PPC, DCM:MeOH; 100:0 to 98:2 to 95:5) to afford the title compound as a tan solid (110 mg, 96%). LCMS (Method H): RT=2.33 min, M+H+=395.

Workup

  1. washThe cartridge was then washed with methanol
  2. washthe desired product was subsequently eluted
  3. customThe product was collected
  4. concentrationconcentrated in vacuo
  5. customThe resultant residue was purified by flash chromatography (Si—PPC, DCM:MeOH; 100:0 to 98:2 to 95:5)

Sources & evidence

ORD record
ord-812a3a83088847de964da3347931bfac
Source dataset
uspto-grants-2012_05
Patent number
US08173650B2

Reaction notes

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