HCID 86696512, compound → HCID 86696513, compound

HRID 1615916Notes

Reaction equation

HRID 1615916 reaction equation
[F:1][C:2]1[CH:3]=[N:4][C:5]([CH:8]2[CH2:10][CH:9]2[CH2:11][NH:12]C(=O)OCC2C=CC=CC=2)=[N:6][CH:7]=1>[Pd].CO>[F:1][C:2]1[CH:7]=[N:6][C:5]([CH:8]2[CH2:10][CH:9]2[CH2:11][NH2:12])=[N:4][CH:3]=1

Participants

4

Reactant 1

HCID 86696512HCID 86696512, compound

Product 1

HCID 86696513HCID 86696513, compoundYield 48.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of benzyl ((2-(5-fluoropyrimidin-2-yl)cyclopropyl)methyl)carbamate (180 mg, 0.597 mmol), 10% palladium on carbon (63 mg) in MeOH (10 mL) was shaken in a Parr shaker under hydrogen (10 psi) for 2 h. The reaction mixture was filtered and the filtrate was concentrated. The residue purified by silica gel chromatography using 0-20% 2.0 M ammonia in MeOH/EtOAc as the eluent to give (2-(5-fluoropyrimidin-2-yl)cyclopropyl)methanamine as a yellowish oil (48 mg, 48%). 1H NMR (400 MHz, CHLOROFORM-d) d 8.40 (s, 2H), 2.81-2.66 (m, 2H), 2.11 (dt, J=8.5, 4.4 Hz, 1H), 1.70-1.58 (m, 1H), 1.30 (bs, 2H, NH2), 1.28 (m, 1H), 0.97 (ddd, J=8.5, 6.0, 4.3 Hz, 1H). LCMS: M+1=168.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customThe residue purified by silica gel chromatography

Sources & evidence

ORD record
ord-f0a328cf115544b790e8cc3496ac0b57
Source dataset
uspto-grants-2014_07
Patent number
US08765767B2

Reaction notes

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