Hydrochloric Acid → 5-(4-chloro-2,3-dihydro-1H-indol-5-yl)-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine 2HCl

HRID 1910099Notes

Reaction equation

[NH2:1][C:2]1[C:3]2[C:10]([C:11]3[C:12]([Cl:27])=[C:13]4[C:17](=[CH:18][CH:19]=3)[N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]4)=[CH:9][N:8]([CH3:28])[C:4]=2[N:5]=[CH:6][N:7]=1.[ClH:29]>>[ClH:27].[ClH:29].[Cl:27][C:12]1[C:11]([C:10]2[C:3]3[C:2]([NH2:1])=[N:7][CH:6]=[N:5][C:4]=3[N:8]([CH3:28])[CH:9]=2)=[CH:19][CH:18]=[C:17]2[C:13]=1[CH2:14][CH2:15][NH:16]2

Participants

Reactant 2

HCID 313Hydrochloric Acid

HCID 668239601,1-dimethylethyl 5-(4-amino-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-4-chloro-2,3-dihydro-1H-indole-1-carboxylate

Product 1

HCID 668235055-(4-chloro-2,3-dihydro-1H-indol-5-yl)-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine 2HClYield 199.9%

Procedure

A suspension of 1,1-dimethylethyl 5-(4-amino-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-4-chloro-2,3-dihydro-1H-indole-1-carboxylate (0.716 g, 1.791 mmol) in HCl (4 M, dioxane) (30 mL, 120 mmol) was stirred at room temperature overnight. LCMS indicated good conversion. The reaction mixture was concentrated to afford 5-(4-chloro-2,3-dihydro-1H-indol-5-yl)-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine 2HCl (667 mg, 1.790 mmol, 100% yield) as an off-white solid. LC-MS (ES) m/z=300 [M+H]+. 1H NMR (400 MHz, DMSO-d6) d ppm 3.05 (t, J=8.59 Hz, 2H), 3.56-3.63 (m, 2H), 3.81-3.98 (m, 8H), 6.55-6.62 (m, 1H), 7.01 (d, J=7.58 Hz, 1H), 7.49 (s, 1H), 8.45 (s, 1H).

Workup

concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record: ord-3aca6a0126f046a2a19de5c923ce2e18
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598156B2

Reaction notes

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