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Hydrochloric Acid → (S)-1-[3-(4-Methoxy-benzyl)-5-(2,2,2-trifluoro-ethoxy)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl]-pyrrolidin-3-ol

HRID 2179102
Notes
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Reaction equation

HRID 2179102 reaction equation
[F:1][C:2]([F:6])([F:5])[CH2:3][OH:4].[H-].[Na+].Cl[C:10]1[N:11]=[C:12]([N:28]2[CH2:32][CH2:31][C@H:30]([OH:33])[CH2:29]2)[C:13]2[N:18]=[N:17][N:16]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=3)[C:14]=2[N:15]=1.Cl>C1COCC1>[CH3:27][O:26][C:23]1[CH:22]=[CH:21][C:20]([CH2:19][N:16]2[C:14]3[N:15]=[C:10]([O:4][CH2:3][C:2]([F:6])([F:5])[F:1])[N:11]=[C:12]([N:28]4[CH2:32][CH2:31][C@H:30]([OH:33])[CH2:29]4)[C:13]=3[N:18]=[N:17]2)=[CH:25][CH:24]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 64092,2,2-TrifluoroethanolHCID 24758Sodium hydrideHCID 89587064(3 S)-1-[5-Chloro-3-[(4-methoxyphenyl)methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol

Product 1

HCID 89586559(S)-1-[3-(4-Methoxy-benzyl)-5-(2,2,2-trifluoro-ethoxy)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl]-pyrrolidin-3-ol

Reagents, catalysts & solvents

1
HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2,2,2-trifluoroethanol (936 mg, 9.35 mmol) in THF was treated with NaH for 1 h at room temperature. (S)-1-[5-Chloro-3-(4-methoxy-benzyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl]-pyrrolidin-3-ol (example 109, c) was added and the mixture was stirred at 100° C. for 2 h. The reaction mixture was poured into 1 M HCl and extracted with EtOAc. The combined organic layers were dried over MgSO4 and concentrated in vacuo to yield the crude title compound which was used in the consecutive step without further purification. MS (m/e): 425.4 (MH+).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8b62a28be5d74363b2f853874cfd99e4
Source dataset
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09067943B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes