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Diisopropylethylamine → 7-(3-Methanesulphonylpyridin-2-yl)-N-(5-(trifluoromethyl)pyridin-2-yl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-amine

HRID 971221
Notes
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Reaction equation

HRID 971221 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10]2[C:11]3[CH2:19][CH2:18][NH:17][CH2:16][C:12]=3[N:13]=[CH:14][N:15]=2)=[N:7][CH:8]=1.Cl[C:23]1[C:28]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:27][CH:26]=[CH:25][N:24]=1.C(N(CC)C(C)C)(C)C>C(#N)C>[CH3:32][S:29]([C:28]1[C:23]([N:17]2[CH2:18][CH2:19][C:11]3[C:10]([NH:9][C:6]4[CH:5]=[CH:4][C:3]([C:2]([F:20])([F:1])[F:21])=[CH:8][N:7]=4)=[N:15][CH:14]=[N:13][C:12]=3[CH2:16]2)=[N:24][CH:25]=[CH:26][CH:27]=1)(=[O:31])=[O:30]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 125137462-Chloro-3-(methanesulfonyl)pyridineHCID 69424206N-(5-(Trifluoromethyl)pyridine-2-yl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-amine

Product 1

HCID 694250497-(3-Methanesulphonylpyridin-2-yl)-N-(5-(trifluoromethyl)pyridin-2-yl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-amineYield 43.1%

Reagents, catalysts & solvents 1

HCID 6342
Acetonitrile
Solvent

Conditions

Temperature
150 °C

Procedure

N-(5-(Trifluoromethyl)pyridine-2-yl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-amine (100 mg, 0.34 mmol) was dissolved in a mixture of acetonitrile (2 mL). To the mixture was added 2-chloro-3-methanesulphonylpyridine (122 mg, 0.68 mmol) and N,N-diisopropylethylamine (0.23 mL, 0.68 mmol). The mixture was heated in a sealed tube at 150° C. in microwave (Model, Personal Chemistry) for 16 h. The solvents were removed under vacuum and the residue was dissolved in ethyl acetate and washed with sat. NaHCO3 and brine. The organic layer was dried over Na2SO4, filtered and evaporated to give a brown residue. The residue was purified by flash chromatography over silica gel using a gradient of ethyl acetate:hexane (0-100%) to give the desired compound as an off-white powder (66 mg).

Workup

  1. customThe solvents were removed under vacuum
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with sat. NaHCO3 and brine
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customto give a brown residue
  8. customThe residue was purified by flash chromatography over silica gel using a gradient of ethyl acetate

Sources & evidence

ORD record
ord-3d190dcfdce146a79af2b02db42e6e9b
Source dataset
uspto-grants-2007_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07312330B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes