Propylamine → 2-(8-((3,4-difluorobenzyl)oxy)-6-oxo-2,3,4,6-tetrahydro-1H-pyrimido[1,6-a]pyrimidin-1-yl)-N-propylacetamide

HRID 930817Notes

Reaction equation

HRID 930817 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][C:24]=1[F:25])[CH2:5][O:6][C:7]1[CH:20]=[C:11]2[N:12]([CH2:16][C:17]([OH:19])=O)[CH2:13][CH2:14][CH2:15][N:10]2[C:9](=[O:21])[N:8]=1.CCN(C(C)C)C(C)C.CN(C(O[N:43]1N=N[C:45]2[CH:46]=CC=N[C:44]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N)CC>O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][C:24]=1[F:25])[CH2:5][O:6][C:7]1[CH:20]=[C:11]2[N:12]([CH2:16][C:17]([NH:43][CH2:44][CH2:45][CH3:46])=[O:19])[CH2:13][CH2:14][CH2:15][N:10]2[C:9](=[O:21])[N:8]=1

Participants

6

Reactant 4

HCID 7852PropylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 90303921HCID 90303921, compound

Product 1

HCID 771074342-(8-((3,4-difluorobenzyl)oxy)-6-oxo-2,3,4,6-tetrahydro-1H-pyrimido[1,6-a]pyrimidin-1-yl)-N-propylacetamideYield 5.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 2-(8-((3,4-difluorobenzyl)oxy)-6-oxo-2,3,4,6-tetrahydro-1H-pyrimido[1,6-a]pyrimidin-1-yl)acetic acid (300 mg, 0.854 mmol), Hunig's base (0.597 mL, 3.42 mmol) and HATU (487 mg, 1.281 mmol) in tetrahydrofuran (10 mL) was added propan-1-amine (76 mg, 1.281 mmol). The reaction mixture was stirred at 20° C. for 2 hours. The solution was concentrated and purified by MDAP, to afford title compound (20 mg, 0.049 mmol, 5.69% yield).

Workup

  1. concentrationThe solution was concentrated
  2. custompurified by MDAP

Sources & evidence

ORD record
ord-21d8ec4e5df34e8583e90869a4db5018
Source dataset
uspto-grants-2016_03
Patent number
US09296755B2

Reaction notes

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