Diisopropylethylamine → HCID 178514075, compound

HRID 32490

Reaction equation

HRID 32490 reaction equation
[NH2:1][C:2]1[N:7]([C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=2)[CH2:6][N:5]=[C:4]2[S:15][CH:16]=[CH:17][C:3]=12.[N-:18]=[C:19]=[O:20].[F:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][C:23]=1N=C=O.C(N(C(C)C)CC)(C)C>CO.C(N(CC)CC)C>[NH2:1][C:2]1[N:7]([C:8]2[CH:9]=[CH:10][C:11]([N:14]([C:23]3[CH:24]=[C:25]([C:28]([F:30])([F:31])[F:29])[CH:26]=[CH:27][C:22]=3[F:21])[C:19]([NH2:18])=[O:20])=[CH:12][CH:13]=2)[CH2:6][N:5]=[C:4]2[S:15][CH:16]=[CH:17][C:3]=12

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 105034IsocyanateHCID 27333802-Fluoro-5-(trifluoromethyl)phenyl isocyanateHCID 178507154HCID 178507154, compound

Product 1

HCID 178514075HCID 178514075, compound

Reagents, catalysts & solvents 1

HCID 22728368Triethylamine methanolSolvent

Procedure

4-Amino-3-(4-aminophenyl)thieno[2,3-d]pyrimidine (0.2 mmoles) was dissolved in 1 mL amine-free DMF and treated with 0.3 mmoles of the isocyanate of choice (2-fluoro-5-trifluoromethyl-phenyl isocyanate) and 0.6 mmoles of diisopropylethylamine for 2 hours at room temperature. The reaction mixture was treated with 0.5 mL 1:1 methanol-triethylamine for half an hour and concentrated to dryness in a Speedvac system, reconstituted in 1 mL DMSO and purified by prep HPLC. The fraction containing the desired product was collected and concentrated to dryness. MH+=448.

Workup

  1. concentrationconcentrated to dryness in a Speedvac system
  2. custompurified by prep HPLC
  3. additionThe fraction containing the desired product
  4. customwas collected
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-8578b14822cf4369b70e5cbd9aec395b
Source dataset
uspto-grants-2008_09
Patent number
US07427623B2

Linked notes

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