Potassium Carbonate → HCID 87353595, compound

HRID 1012982Notes

Reaction equation

[CH2:1]([O:8][C:9]1[C:14](=[O:15])[N:13]2[CH2:16][CH2:17][NH:18][C:19]([CH3:21])([CH3:20])[C:12]2=[N:11][C:10]=1[C:22]([NH:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=1)=[O:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:40][C:41]#[N:42]>CN(C=O)C>[CH2:1]([O:8][C:9]1[C:14](=[O:15])[N:13]2[CH2:16][CH2:17][N:18]([CH2:40][C:41]#[N:42])[C:19]([CH3:21])([CH3:20])[C:12]2=[N:11][C:10]=1[C:22]([NH:24][CH2:25][C:26]1[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=1)=[O:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 3-(benzyloxy)-N-(4-fluorobenzyl)-9,9-dimethyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrazino[1,2-a]pyrimidine-2-carboxamide (see Example 3, Step 1), K2CO3 (2 eq.) and bromoacetonitrile (2 eq.) in DMF was heated at 70° C. overnight and was then cooled to room temperature. The solvent was removed under reduced pressure and the residue was taken up in EtOAc, washed with brine, dried (Na2SO4) and concentrated to yield the crude nitrile which was used in the next step without further purification. 1H NMR (300 MHz, d6-DMSO) δ 8.9 (t, J=6.2 Hz, 1H), 7.26-7.41 (m, 7H), 7.06 (t, J=8.8 Hz, 2H), 5.06 (s, 2H), 4.41 (d, J=6.2 Hz, 2H), 3.96 (s, 2H), 3.89 (t, J=5.2 Hz, 2H), 3.15 (t, J=5.2 Hz, 2H), 1.53 (s, 6H); MS (ES) C26H26FN5O3 requires 475. Found: 476 (M+H+).

Workup

temperaturewas then cooled to room temperature
customThe solvent was removed under reduced pressure
washwashed with brine
dry with materialdried (Na2SO4)
concentrationconcentrated

Sources & evidence

ORD record: ord-a1ceaaa70fbf4e9b9b85970cdb9d2b0d
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07981879B2

Reaction notes

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