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Hydrochloric Acid → 3-pyridylmethyl N-[4-(4-amino-7-tetrahydro-2H-4-pyranyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methoxyphenyl]carbamate hydrochloride

HRID 51545
Notes
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Reaction equation

HRID 51545 reaction equation
[NH2:1][C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18](=[O:27])[O:19][CH2:20][C:21]4[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=4)=[C:13]([O:28][CH3:29])[CH:12]=3)=[CH:9][N:8]([CH:30]3[CH2:35][CH2:34][O:33][CH2:32][CH2:31]3)[C:4]=2[N:5]=[CH:6][N:7]=1.[ClH:36]>C(OCC)(=O)C.CCOCC>[ClH:36].[NH2:1][C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18](=[O:27])[O:19][CH2:20][C:21]4[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=4)=[C:13]([O:28][CH3:29])[CH:12]=3)=[CH:9][N:8]([CH:30]3[CH2:35][CH2:34][O:33][CH2:32][CH2:31]3)[C:4]=2[N:5]=[CH:6][N:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 227362193-pyridylmethyl N-[4-(4-amino-7-tetrahydro-2H-4-pyranyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methoxyphenyl]carbamate

Product 1

HCID 227363123-pyridylmethyl N-[4-(4-amino-7-tetrahydro-2H-4-pyranyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methoxyphenyl]carbamate hydrochloride

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent
HCID 8857
Ethyl Acetate
Solvent

Procedure

3-Pyridylmethyl N-[4-(4-amino-7-tetrahydro-2H-4-pyranyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methoxyphenyl]carbamate (12 mg, 0.025 mmol) was dissolved in ethyl acetate (2.0 mL). 1.0N HCl in ether (1 mL) was added slowly. The precipatate was collected through filtration under nitrogen to give 3-pyridylmethyl N-[4-(4-amino-7-tetrahydro-2H-4-pyranyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methoxyphenyl]carbamate hydrochloride(13 mg, 0.25 mmol). 1H NMR (DMSO-d6) δ 1.91 (m, 2H), 2.17 (m, 2H), 3.54 (m, 2H), 3.87 (s, 3H), 4.03 (m, 2H), 4.97 (m, 1H), 5.23 (s, 2H), 7.05 (d, J=8.2 Hz, 1H), 7.13 (s, 1H), 7.51 (m, 1H), 7.81 (d, J=8.2 Hz, 1H), 7.84 (s, 1H), 7.95 (m, 1H), 8.42 (s, 1H), 8.60 (s, 1H), 8.71 (s, 1H), 8.82 (s, 1H). LC/MS MH+=475.

Workup

  1. filtrationThe precipatate was collected through filtration under nitrogen

Sources & evidence

ORD record
ord-c5c7cbb3195f47909d2a00484a71bb13
Source dataset
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06713474B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes