Formaldehyde → HCID 178492187, compound

HRID 510969Notes

Reaction equation

HRID 510969 reaction equation
C=O.O.[Cl:4][C:5]1[C:6]([CH3:31])=[C:7]([CH:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[C:8]([O:23][CH3:24])=[C:9]([CH:11]([NH:13][C:14]2[N:22]=[CH:21][N:20]=[C:19]3[C:15]=2[N:16]=[CH:17][NH:18]3)[CH3:12])[CH:10]=1.[CH3:32]CN(C(C)C)C(C)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[Cl:4][C:5]1[C:6]([CH3:31])=[C:7]([CH:25]2[CH2:30][CH2:29][N:28]([CH3:32])[CH2:27][CH2:26]2)[C:8]([O:23][CH3:24])=[C:9]([CH:11]([NH:13][C:14]2[N:22]=[CH:21][N:20]=[C:19]3[C:15]=2[N:16]=[CH:17][NH:18]3)[CH3:12])[CH:10]=1

Participants

7

Reactant 5

HCID 712FormaldehydeHCID 962WaterHCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 178492186N-[1-(5-Chloro-2-methoxy-4-methyl-3-piperidin-4-ylphenyl)ethyl]-9H-purin-6-amine

Product 1

HCID 178492187HCID 178492187, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

12.0 M Formaldehyde in water (0.4 mL, 5 mmol) was added to a mixture of N-[1-(5-chloro-2-methoxy-4-methyl-3-piperidin-4-ylphenyl)ethyl]-9H-purin-6-amine (200 mg, 0.5 mmol) and DIPEA (0.35 mL, 2.0 mmol) in methylene chloride (5 mL) at 0° C. The reaction was stirred for 10 minutes, and after this time sodium triacetoxyborohydride (160 mg, 0.75 mmol) was added. The reaction was stirred at 0° C. for 1 hour. The mixture was purified on RP-HPLC (XBridge C18 Column, eluting with a gradient of acetonitrile in water with 0.2% ammonium hydroxide, at flow rate of 30 mL/min) to give the desired product. LCMS calculated for C21H28ClN6O (M+H)+: m/z=415.2. found: 415.3. 1H NMR (DMSO-d6, 500 MHz) δ 9.67 (1H, br s), 8.72 (1H, br s), 8.35 (2H, s), 7.51 (1H, s), 5.75 (1H, m), 3.88 (3H, s), 3.49 (2H, m), 3.34 (1H, m), 3.12 (2H, m), 2.81 (1.5H, s), 2.80 (1.5H, s), 2.44-2.31 (2H, m), 2.36 (3H, s), 1.79 (2H, m), 1.49 (3H, d, J=6.5 Hz) ppm.

Workup

  1. stirringThe reaction was stirred at 0° C. for 1 hour
  2. customThe mixture was purified on RP-HPLC (XBridge C18 Column
  3. washeluting with a gradient of acetonitrile in water with 0.2% ammonium hydroxide, at flow rate of 30 mL/min)

Sources & evidence

ORD record
ord-2ecce030d4ed4b75963d40e38b2520c5
Source dataset
uspto-grants-2015_08
Patent number
US09096600B2

Reaction notes

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