2-Methyl-2-butanol → HCID 178517910, compound

HRID 1186110Notes

Reaction equation

HRID 1186110 reaction equation
[N:1]1[C:6]2[CH2:7][CH2:8][NH:9][CH2:10][CH2:11][C:5]=2[C:4]([OH:12])=[N:3][CH:2]=1.F[C:14]1[C:19]([C:20]([F:23])([F:22])[F:21])=[CH:18][CH:17]=[CH:16][N:15]=1.CCN(C(C)C)C(C)C.C(O)(CC)(C)C>>[F:21][C:20]([F:23])([F:22])[C:19]1[C:14]([N:9]2[CH2:10][CH2:11][C:5]3[C:4]([OH:12])=[N:3][CH:2]=[N:1][C:6]=3[CH2:7][CH2:8]2)=[N:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 4

HCID 64052-Methyl-2-butanolHCID 81531DiisopropylethylamineHCID 27832962-Fluoro-3-(trifluoromethyl)pyridineHCID 178517914HCID 178517914, compound

Product 1

HCID 178517910HCID 178517910, compoundYield 34%

Procedure

A solution of 6,7,8,9-tetrahydro-5H-pyrimido[4,5-d]azepin-4-ol (353 mg, 1.76 mmol), 2-fluoro-3-trifluoromethyl-pyridine (582 mg, 3.53 mmol), iPr2NEt (0.9 mL, 5.28 mmol), and t-amyl alcohol (5 mL) was heated in a microwave at 180° C. for 5 h. The mixture was concentrated, diluted with water, and extracted with EtOAc. The combined organic layers were dried (Na2SO4) and concentrated to give the title compound (185 mg, 34%), which was used in the next step without further purification.

Workup

  1. concentrationThe mixture was concentrated
  2. additiondiluted with water
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7659769c5ed445ed82c22cfef73c51bf
Source dataset
uspto-grants-2014_03
Patent number
US08673895B2

Reaction notes

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