Hydrochloric Acid → 5-{7-(azetidin-3-yl)-2-[(3S)-3-methylmorpholin-4-yl]-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl}pyrimidin-2-amine dihydrochloride

HRID 1775463Notes

Reaction equation

HRID 1775463 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]([CH:24]4[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:35].O1CCOCC1>CO.C1(C)C=CC=CC=1>[ClH:35].[ClH:35].[NH:26]1[CH2:27][CH:24]([N:21]2[C:10]3[N:11]=[C:12]([N:14]4[CH2:19][CH2:18][O:17][CH2:16][C@@H:15]4[CH3:20])[N:13]=[C:8]([C:5]4[CH:4]=[N:3][C:2]([NH2:1])=[N:7][CH:6]=4)[C:9]=3[CH2:23][CH2:22]2)[CH2:25]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 118436691tert-butyl 3-{4-(2-aminopyrimidin-5-yl)-2-[(3S)-3-methylmorpholin-4-yl]-5,6-dihydro-7H-pyrrolo[2,3-d]pyrimidin-7-yl}azetidine-1-carboxylate

Product 1

HCID 1184362655-{7-(azetidin-3-yl)-2-[(3S)-3-methylmorpholin-4-yl]-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl}pyrimidin-2-amine dihydrochloride

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

To a solution of tert-butyl 3-{4-(2-aminopyrimidin-5-yl)-2-[(3S)-3-methylmorpholin-4-yl]-5,6-dihydro-7H-pyrrolo[2,3-d]pyrimidin-7-yl}azetidine-1-carboxylate (760 mg, 1.62 mmol) in methanol (8 mL), was added 4 N HCl in 1,4-dioxane (8 mL, 32 mmol). The reaction was stirred at room temperature for 1 h. The mixture was diluted with toluene and the solvent was removed under reduced pressure to give a foamy residue. The residue was triturated in acetone to get a free flowing tan solid which was collected by filtration to give the title compound in quantitative yield. The material was taken directly in the next step without purification. 1H NMR (400 MHz, CD3OD) δ 8.78 (br s, 2 H), 5.32 (br s, 1 H), 4.62 (br s, 3 H), 4.34 (br s, 2 H), 4.19-3.99 (m, 4 H), 3.85-3.72 (m, 2 H), 3.64-3.46 (m, 2 H), 3.23 (br s, 2 H), 1.41 (d, J=5.5 Hz, 3 H).

Workup

  1. customthe solvent was removed under reduced pressure
  2. customto give a foamy residue
  3. customThe residue was triturated in acetone
  4. customto get
  5. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-1420c02aa40d4bfdb249761e407ebb5c
Source dataset
uspto-grants-2016_02
Patent number
US09260439B2

Reaction notes

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