Phosgene → HCID 22125087, compound

HRID 1858286Notes

Reaction equation

HRID 1858286 reaction equation
[Br:1][C:2]1[CH:32]=[CH:31][CH:30]=[CH:29][C:3]=1[NH:4][CH2:5][C:6]1[C:7]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([CH2:21][O:22][CH:23]3[CH2:28][CH2:27][CH2:26][CH2:25][O:24]3)=[CH:17][CH:16]=2)=[N:8][C:9]([S:12][CH3:13])=[N:10][CH:11]=1.C(N(CC)CC)C.[C:40](Cl)(Cl)=[O:41]>O1CCCC1.C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:32]=[CH:31][CH:30]=[CH:29][C:3]=1[N:4]1[CH2:5][C:6]2[C:7](=[N:8][C:9]([S:12][CH3:13])=[N:10][CH:11]=2)[N:14]([C:15]2[CH:16]=[CH:17][C:18]([CH2:21][O:22][CH:23]3[CH2:28][CH2:27][CH2:26][CH2:25][O:24]3)=[CH:19][CH:20]=2)[C:40]1=[O:41]

Participants

6

Reactant 3

HCID 6371PhosgeneHCID 8471TriethylamineHCID 22125151HCID 22125151, compound

Product 1

HCID 22125087HCID 22125087, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution containing 0.93 g (1.8 mmol) of 5-(2-bromoanilino)methyl-4-[4-(tetrahydropyran-2-yloxymethyl)phenyl]amino-2-methylthiopyrimidine and 0.5 ml (3.61 mmol) of triethylamine in 5 ml of anhydrous tetrahydrofuran was added dropwise to 1.9 ml (3.61 mmol) of a 20% solution of phosgene in toluene dissolved in 5 ml of tetrahydrofuran at 0° C. under an atmosphere of nitrogen. The reaction was stirred at 0° C. for a further 60 minutes then evaporated. The residue was partitioned between ethyl acetate (10 ml) and 2M hydrochloric acid (10 ml), the ethyl acetate layer was separated then washed with saturated aqueous sodium bicarbonate (10 ml), dried over magnesium sulfate, filtered and evaporated to give 0.945 g (97%) of 3-(2-bromophenyl)-3,4-dihydro-1-[4-(tetrahydropyran-2-yloxymethyl)phenyl]-7-methylthio-pyrimido[4,5-d]pyrimidin-2(1H)-one as a yellow gum. [Mass spectrum (ESI) MH+ =541].

Workup

  1. customthen evaporated
  2. customThe residue was partitioned between ethyl acetate (10 ml) and 2M hydrochloric acid (10 ml)
  3. customthe ethyl acetate layer was separated
  4. washthen washed with saturated aqueous sodium bicarbonate (10 ml)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-cacda787484f4433a89182bfc1623ad3
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

Loading…