Triethylamine → HCID 58109314, compound

HRID 2037399Notes

Reaction equation

HRID 2037399 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][CH2:9][CH2:10][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([OH:13])[CH3:12])[N:3]=1.[CH3:20][CH2:21][N:22](CC)CC.Cl[C:28](Cl)([O:30]C(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl>[Cl:1][C:2]1[N:3]=[C:4]([N:8]2[CH2:9][CH2:10][C:11]([CH3:12])([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[O:13][C:28]2=[O:30])[CH:20]=[CH:21][N:22]=1.[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([N:8]2[CH2:9][CH2:10][C:11]([CH3:12])([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[O:13][C:28]2=[O:30])[N:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 86649945HCID 86649945, compound

Product 2

HCID 25182014HCID 25182014, compoundYield 9%HCID 58109314HCID 58109314, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-(4-chloro-pyrimidin-2-ylamino)-2-phenyl-butan-2-ol (450 mg, 1.6 mmol) and Et3N (508 mg, 4.8 mmol) in CH2Cl2 (2 ml) was added dropwise a solution of triphosgene (159 mg, 0.54 mmol) in CH2Cl2 slowly at 0° C. under nitrogen atmosphere. The mixture was stirred at rt overnight. The mixture was concentrated to give the crude product, which was purified by TLC and preparative HPLC to afford 3-(2-chloropyrimidin-4-yl)-6-methyl-6-phenyl-1,3-oxazinan-2-one (250 mg, 52%) 1H NMR (CDCl3, 400 MHZ): δ=1.73 (s, 3H), 2.38 (m, 1H), 2.63 (m, 1H), 3.49 (m, 1H), 4.2 (m, 1H), 7.36 (m, 5H), 8.28 (m, 1H), 8.52 (m, 1H) and 3-(4-chloropyrimidin-2-yl)-6-methyl-6-phenyl-1,3-oxazinan-2-one (20 mg, 9%) [Example 57]. 1H NMR (CDCl3, 400 MHZ): δ=1.73 (s, 3H), 2.4 (m, 1H), 2.58 (m, 1H), 3.47 (m, 1H), 4.13 (m, 1H), 7.06 (m, 5H), 7.16-7.55 (m, 5H), 8.54 (m, 1H).

Workup

  1. concentrationThe mixture was concentrated
  2. customto give the crude product, which
  3. customwas purified by TLC and preparative HPLC

Sources & evidence

ORD record
ord-2681ba75038541b6b9a7f73bef2b6fff
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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