Hydrochloric Acid → HCID 59548351, compound

HRID 1811867Notes

Reaction equation

HRID 1811867 reaction equation
[O:1]1CCO[CH:2]1[C:6]1[CH:7]=[C:8]([C:21]2[N:29]=[C:28]([CH3:30])[N:27]=[C:26]3[C:22]=2[N:23]=[CH:24][N:25]3[CH:31]2[CH2:36][CH2:35][CH2:34][CH2:33][O:32]2)[C:9]([NH:12][C:13]2[CH:14]=[N:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=2)=[N:10][CH:11]=1.Cl>O1CCCC1>[CH3:20][O:19][C:16]1[N:15]=[CH:14][C:13]([NH:12][C:9]2[C:8]([C:21]3[N:29]=[C:28]([CH3:30])[N:27]=[C:26]4[C:22]=3[N:23]=[CH:24][N:25]4[CH:31]3[CH2:36][CH2:35][CH2:34][CH2:33][O:32]3)=[CH:7][C:6]([CH:2]=[O:1])=[CH:11][N:10]=2)=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 666106795-(1,3-dioxolan-2-yl)-N-(6-methoxypyridin-3-yl)-3-(2-methyl-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)pyridin-2-amine

Product 1

HCID 59548351HCID 59548351, compoundYield 61.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

5-(1,3-Dioxolan-2-yl)-N-(6-methoxypyridin-3-yl)-3-(2-methyl-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)pyridin-2-amine (3.042 g, 6.21 mmol) was dissolved in tetrahydrofuran (50 mL) and then 2.0 M hydrochloric acid (15.5 mL, 31.0 mmol) was added via syringe, followed by a THF rinse (1.5 mL). The reaction was stirred at room temperature for 20 minutes, diluted with water (20 mL), and filtered. The solid was washed with water, collected, and dried under high vacuum over the weekend to afford 6-(6-methoxypyridin-3-ylamino)-5-(2-methyl-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)nicotinaldehyde (1.7 g, 61% yield). MS (ESI pos. ion) m/z 446 (M+H)+. 1H NMR (CDCl3, 400 MHz) δ 13.33 (s, 1H), 10.29 (d, J=2.15 Hz, 1H), 10.00 (s, 1H), 8.78 (d, J=1.96 Hz, 1H), 8.48 (d, J=2.74 Hz, 1H), 8.35 (s, 1H), 8.25 (dd, J=8.8 Hz, 2.74 Hz, 1H), 6.84 (d, J=8.8 Hz, 1H), 5.89 (dd, J=10.47 Hz, 2.05 Hz, 1H), 4.23 (d, J=11.74 Hz, 1H), 3.98 (s, 3H), 3.88-3.82 (m, 1H), 2.93 (s, 3H), 2.23-2.03 (m, 3H), 1.90-1.65 (m, 3H).

Workup

  1. washrinse (1.5 mL)
  2. additiondiluted with water (20 mL)
  3. filtrationfiltered
  4. washThe solid was washed with water
  5. customcollected
  6. customdried under high vacuum over the weekend

Sources & evidence

ORD record
ord-f9d35767d2264ddea63c5b92ea2c681f
Source dataset
uspto-grants-2013_01
Patent number
US08362241B2

Reaction notes

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