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Diisopropylethylamine → 2-(2-amino-5-formyl-6-methylsulfanyl-pyrimidin-4-ylamino)-N-(3-trifluoromethyl-phenyl)-acetamide

HRID 1160111
Notes
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Reaction equation

HRID 1160111 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][C:10]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=2)=[O:11])[C:5]([CH:23]=[O:24])=[C:4](Cl)[N:3]=1.CCN(C(C)C)C(C)C.[CH3:35][S-:36].[Na+]>C1COCC1>[NH2:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][C:10]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=2)=[O:11])[C:5]([CH:23]=[O:24])=[C:4]([S:36][CH3:35])[N:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 4378561Sodium methanethiolateHCID 112917662-(2-Amino-6-chloro-5-formyl-pyrimidin-4-ylamino)-N-(3-trifluoromethyl-phenyl)-acetamide

Product 1

HCID 111766082-(2-amino-5-formyl-6-methylsulfanyl-pyrimidin-4-ylamino)-N-(3-trifluoromethyl-phenyl)-acetamideYield 92.7%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Conditions

Temperature
0 °C

Procedure

To a round bottom flask is added 2-(2-amino-6-chloro-5-formyl-pyrimidin-4-ylamino)-N-(3-trifluoromethyl-phenyl)-acetamide (80.0 mg, 0.21 mmol, 1.0 eq.), THF (5.0 mL), and DIEA (0.036 mL, 0.21 mmol, 1.0 eq.). The flask was then cooled to 0° C. before adding sodium thiomethoxide (16.0 mg, 0.23 mmol, 1.1 eq.). The reaction was warmed to RT and stirred for 3 hrs before quenching with H2O (10 mL) and EtOAc (50 mL). The EtOAc layer washed with brine, dried with Na2SO4, and concentrated to give pure 2-(2-amino-5-formyl-6-methylsulfanyl-pyrimidin-4-ylamino)-N-(3-trifluoromethyl-phenyl)-acetamide as a yellow solid (75.0 mg, 92%). LC/MSD (HP Series 1100 MSD): Expected MW: 385, Observed M+H, 386.1, Retention time: 1.58 min. ANALYTICAL HPLC: >95%, Retention time: 4.30 min (8 minute run). 1H-NMR (d6-DMSO): 10.48 (s, 1H), 9.98 (s, 1H), 9.35 (t, 1H), 8.10 (s, 1H), 7.80 (d, 1H), 7.59 (t, 1H), 7.41 (m, 2H), 7.25 (br s, 1H), 4.25 (d, 2H), (3 thiomethyl protons are buried under DMSO peak) ppm. 1H-NMR (d-MeOH): 10.0 (s, 1H), 8.00 (s, 1H), 7.78 (d, 1H), 7.50 (t, 1H), 7.39 (d, 1H), 4.33 (s, 2H), 2.51 (s, 3H) ppm.

Workup

  1. temperatureThe reaction was warmed to RT
  2. custombefore quenching with H2O (10 mL) and EtOAc (50 mL)
  3. washThe EtOAc layer washed with brine
  4. dry with materialdried with Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b07f227f1e8241e4a153e3038b825fa8
Source dataset
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07816353B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes