Trifluoroacetic acid → HCID 118598623, compound

HRID 1050380Notes

Reaction equation

HRID 1050380 reaction equation
C(OC([N:8]([C:16]1[C:21]([F:22])=[C:20]([NH:23][C:24]([CH:26]2[CH2:28][CH2:27]2)=[O:25])[N:19]=[CH:18][N:17]=1)C(=O)OC(C)(C)C)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:8][C:16]1[N:17]=[CH:18][N:19]=[C:20]([NH:23][C:24]([CH:26]2[CH2:28][CH2:27]2)=[O:25])[C:21]=1[F:22]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 118598740HCID 118598740, compound

Product 1

HCID 118598623HCID 118598623, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl N-tert-butoxycarbonyl-N-[6-(cyclopropanecarbonylamino)-5-fluoro-pyrimidin-4-yl]carbamate (4, 0.89 g, 2.25 mmol) in dichloromethane (20 mL), trifluoroacetic acid (20 mL, 2.25 mmol) was added at 0° C. and stirred the reaction mass at room temperature for 16 h. After completion the reaction, trifluoroacetic acid was distilled and the crude compound was basified with liquid ammonia. The solid precipitated out was filtered and dried to afford N-(6-amino-5-fluoro-pyrimidin-4-yl)cyclopropanecarboxamide (5) as off white solid. Yield: 0.4 g, 90%; MS (ESI) m/z 197.06 [M+1]+; 1H NMR (400 MHz, DMSO-d6) δ 10.37 (s, 1H), 7.99 (s, 1H), 7.16 (s, 2H), 7.04 (s, 1H), 2.06 (m, 1H), 0.82-0.78 (m, 4H).

Workup

  1. distillationwas distilled
  2. customThe solid precipitated out
  3. filtrationwas filtered
  4. customdried

Sources & evidence

ORD record
ord-66d0f76b18b5469b817c6eaff05e623c
Source dataset
uspto-grants-2016_07
Patent number
US09382248B2

Reaction notes

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