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Triethylamine → 1-(2-Chloro-6-((2,2,2-trifluoroethoxy)methyl)pyrimidin-4-ylamino)-2-methylpropan-2-ol

HRID 59107
Notes
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Reaction equation

HRID 59107 reaction equation
Cl.[NH2:2][CH2:3][C:4]([CH3:7])([OH:6])[CH3:5].C(N(CC)CC)C.[Cl:15][C:16]1[N:21]=[C:20](Cl)[CH:19]=[C:18]([CH2:23][O:24][CH2:25][C:26]([F:29])([F:28])[F:27])[N:17]=1>CO.C(#N)C>[Cl:15][C:16]1[N:21]=[C:20]([NH:2][CH2:3][C:4]([CH3:7])([OH:6])[CH3:5])[CH:19]=[C:18]([CH2:23][O:24][CH2:25][C:26]([F:29])([F:27])[F:28])[N:17]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 123861811-Amino-2-methyl-propan-2-ol hydrochlorideHCID 1178209122,4-Dichloro-6-((2,2,2-trifluoroethoxy)methyl)pyrimidine

Product 1

HCID 1178210421-(2-Chloro-6-((2,2,2-trifluoroethoxy)methyl)pyrimidin-4-ylamino)-2-methylpropan-2-olYield 32%

Reagents, catalysts & solvents 2

HCID 887
Methanol
Solvent
HCID 6342AcetonitrileSolvent

Procedure

1-Amino-2-methylpropan-2-ol hydrochloride (221 mg, 1.76 mmol) was suspended in MeOH (2 mL). Triethylamine (0.147 mL, 1.06 mmol) was added and the suspension was filtered. The filtrate was added to an ice-cold solution of 2,4-dichloro-6-((2,2,2-trifluoroethoxy)methyl)-pyrimidine (92 mg, 0.35 mmol) in acetonitrile (2 mL). The mixture was stirred for 1 h at rt. The mixture was purified by preparative HPLC to give the title compound (35 mg, 32%).

Workup

  1. filtrationthe suspension was filtered
  2. customThe mixture was purified by preparative HPLC

Sources & evidence

ORD record
ord-bf500ce66b424f97b4f9bdfd3fce0bff
Source dataset
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09439904B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes