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

HRID 1922857Notes

Reaction equation

HRID 1922857 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.Cl.Cl.[N:21]1([C:27]([CH3:32])([CH3:31])[C:28]([NH2:30])=[O:29])[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]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:24]3[CH2:23][CH2:22][N:21]([C:27]([CH3:32])([CH3:31])[C:28]([NH2:30])=[O:29])[CH2:26][CH2:25]3)=[CH:8][C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 223148092-Methyl-2-(piperazin-1-yl)propanamide dihydrochlorideHCID 568337422-Chloro-4-morpholinofuro[3,2-d]pyrimidine-6-carbaldehyde

Product 1

HCID 596055422-[4-(2-Chloro-4-morpholin-4-ylfuro[3,2-d]pyrimidin-6-ylmethyl)piperazin-1-yl]isobutyramideYield 82.3%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of 2-chloro-4-morpholin-4-yl-furo[3,2-d]pyrimidine-6-carbaldehyde (300 mg, 1.12 mmol) and 2-piperazin-1-ylisobutyramide dihydrochloride (327 mg, 1.33 mmol) in DCE (12 mL) was stirred at ambient temperature for 1 h. Sodium triacetoxyborohydride (358 mg, 1.69 mmol) was added and the mixture stirred for 6 h, then loaded onto an Isolute® SCX-2 cartridge (25 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; gradient from 100:0 to 90:10) to afford the title compound as a tan solid (390 mg, 82%). LCMS (Method H): RT=2.39 min, M+H+=423

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; gradient from 100:0 to 90:10)

Sources & evidence

ORD record
ord-23002491958c46cab1f620b21d8ed220
Source dataset
uspto-grants-2012_05
Patent number
US08173650B2

Reaction notes

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