Hydrochloric Acid → HCID 118436287, compound

HRID 1775480Notes

Reaction equation

HRID 1775480 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[C:9]3[CH2:23][CH2:22][N:21]([C@@:24]4([CH3:36])[CH2:28][CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25]4)[C:10]=3[N:11]=[C:12]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][C@@H:15]3[CH3:20])[N:13]=2)=[CH:4][N:3]=1.[ClH:37].O1CCOCC1>CO.C1(C)C=CC=CC=1>[ClH:37].[CH3:20][C@H:15]1[CH2:16][O:17][CH2:18][CH2:19][N:14]1[C:12]1[N:13]=[C:8]([C:5]2[CH:4]=[N:3][C:2]([NH2:1])=[N:7][CH:6]=2)[C:9]2[CH2:23][CH2:22][N:21]([C@@:24]3([CH3:36])[CH2:28][CH2:27][NH:26][CH2:25]3)[C:10]=2[N:11]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 118436211HCID 118436211, compound

Product 1

HCID 118436287HCID 118436287, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

To a flask containing tert-butyl(3S)-3-{4-(2-aminopyrimidin-5-yl)-2-[(3S)-3-methylmorpholin-4-yl]-5,6-dihydro-7H-pyrrolo[2,3-d]pyrimidin-7-yl}-3-methylpyrrolidine-1-carboxylate (3290 mg, 6.625 mmol) in 31 mL MeOH was added 4 N HCl in dioxane (33 mL, 132 mmol) dropwise at 0° C. and the mixture was stirred at room temperature for 2 h. The mixture was diluted with toluene and concentrated. Additional toluene was added and the solution was concentrated to give the title compound (3.73 g, >99%) as a yellow foam. 1H NMR (400 MHz, DMSO-d6) δ 9.62 (br s, 2 H), 8.69 (s, 2 H), 7.33-7.11 (m, 2H), 4.63-4.52 (m, 1 H), 4.20 (d, J=11.5 Hz, 1 H), 4.03-3.89 (m, 2 H), 3.83-3.18 (m, 10 H), 3.14-3.03 (m, 2 H), 2.71-2.55 (m, 1 H), 2.20-2.04 (m, 1 H), 1.48 (s, 3 H), 1.28 (d, J=6.7 Hz, 3 H). m/z (APCI+) for C20H28N8O 397.5 (M+H)+.

Workup

  1. concentrationconcentrated
  2. additionAdditional toluene was added
  3. concentrationthe solution was concentrated

Sources & evidence

ORD record
ord-d5d86982998e436fbf17c2a6fbe5d2c1
Source dataset
uspto-grants-2016_02
Patent number
US09260439B2

Reaction notes

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