Acetic Acid → HCID 59605971, compound

HRID 1922801Notes

Reaction equation

HRID 1922801 reaction equation
[CH2:1]([C:3]1[N:7]([C:8]2[N:16]=[C:15]3[C:11]([N:12]=[C:13]([CH:23]=O)[N:14]3[CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][O:18]3)=[C:10]([N:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)[N:9]=2)[C:6]2[CH:31]=[CH:32][CH:33]=[CH:34][C:5]=2[N:4]=1)[CH3:2].Cl.[O:36]1[CH2:41][CH2:40][CH:39]([CH:42]2[CH2:45][NH:44][CH2:43]2)[CH2:38][CH2:37]1.COC(OC)OC.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH2:1]([C:3]1[N:7]([C:8]2[N:16]=[C:15]3[C:11]([N:12]=[C:13]([CH2:23][N:44]4[CH2:45][CH:42]([CH:39]5[CH2:40][CH2:41][O:36][CH2:37][CH2:38]5)[CH2:43]4)[N:14]3[CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][O:18]3)=[C:10]([N:25]3[CH2:26][CH2:27][O:28][CH2:29][CH2:30]3)[N:9]=2)[C:6]2[CH:31]=[CH:32][CH:33]=[CH:34][C:5]=2[N:4]=1)[CH3:2]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 9005Trimethyl orthoformateHCID 5049666Sodium triacetoxyborohydrideHCID 177856433-(oxan-4-yl)azetidine hydrochlorideHCID 59606174HCID 59606174, compound

Product 1

HCID 59605971HCID 59605971, compoundYield 126.4%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A 10 mL round-bottomed flask was charged with a solution of 2-(2-ethylbenzoimidazol-1-yl)-6-morpholin-4-yl-9-(tetrahydropyran-2-yl)-9H-purine-8-carbaldehyde (0.22 g, 0.48 mmol), 3-(tetrahydropyran-4-yl)azetidine hydrochloride (0.093 g, 0.53 mmol) in DCE (5 mL), trimethoxymethane (0.518 mL, 4.8 mmol) and acetic acid (0.03 mL, 0.48 mmol). The reaction mixture was stirred for 4 h at room temperature. Sodium triacetoxyborohydride (0.152 g, 0.72 mmol) was added and the reaction mixture was stirred for a further 72 h at room temperature. The suspension was partitioned between DCM and water; the organic layer was separated and washed with brine, dried with sodium sulphate and concentrated to give 2-(2-Ethylbenzoimidazol-1-yl)-6-morpholin-4-yl-9-(tetrahydropyran-2-yl)-8-[3-(tetrahydropyran-4-yl)azetidin-1-ylmethyl]-9H-purine as an orange oil (0.356 g, 99%). LCMS (Method A): RT=2.97 min, [M+H]+ 587.4

Workup

  1. stirringthe reaction mixture was stirred for a further 72 h at room temperature
  2. customThe suspension was partitioned between DCM and water
  3. customthe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried with sodium sulphate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-65b6f59a66294d3fa1124ceeaaf39d20
Source dataset
uspto-grants-2012_05
Patent number
US08173650B2

Reaction notes

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