6-chloro-2-N,4-N-dipropyl-1,3,5-triazine-2,4-diamine → 6-[1,2]oxazinan-2-yl-N,N'-dipropyl-[1,3,5]triazine-2,4-diamine

HRID 530060Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][CH3:11])[N:5]=[C:4]([NH:12][CH2:13][CH2:14][CH3:15])[N:3]=1.C(N(C(C)C)C(C)C)C.Cl.[O:26]1[CH2:31][CH2:30][CH2:29][CH2:28][NH:27]1.C([O-])(O)=O.[Na+]>O1CCCC1>[O:26]1[CH2:31][CH2:30][CH2:29][CH2:28][N:27]1[C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][CH3:11])[N:5]=[C:4]([NH:12][CH2:13][CH2:14][CH3:15])[N:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

An ACE® pressure tube was charged with 2-chloro-N-(4,6-bis-(n-propylamino)-[1,3,5]triazine (XXXIV) (1.50 g, 6.53 mmol), N-ethyldiisopropylamine (19.59 mmol), 1,2-oxazinane hydrochloride (1.61 g, 13.06 mmol) and tetrahydrofuran. The reaction mixture was heated at 100° C. for 2 h, then cooled and poured into saturated NaHCO3 solution (50 mL). The suspension was extracted with EtOAc (3×25 mL). The combined organic extracts were washed with water (50 mL), brine (50 mL) and dried over Na2SO4. The solvent was removed under reduced pressure and the crude product was purified by flash column chromatography using gradient elution from CH2Cl2/EtOH (99:1) to CH2Cl2/EtOH (95:5) to yield 6-[1,2]oxazinan-2-yl-N,N′-dipropyl-[1,3,5]triazine-2,4-diamine (LVII) (1.63 g, 89%). ESI-MS (m/z): 281 [M+H]+.

Workup

temperaturecooled
extractionThe suspension was extracted with EtOAc (3×25 mL)
washThe combined organic extracts were washed with water (50 mL), brine (50 mL)
dry with materialdried over Na2SO4
customThe solvent was removed under reduced pressure
customthe crude product was purified by flash column chromatography
washelution from CH2Cl2/EtOH (99:1) to CH2Cl2/EtOH (95:5)

Sources & evidence

ORD record: ord-05129805e29540849e1a872ada95a143
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09351972B2

Reaction notes

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