Phosgene → HCID 22125179, compound

HRID 1858269Notes

Reaction equation

HRID 1858269 reaction equation
[Br:1][C:2]1[CH:33]=[CH:32][CH:31]=[CH:30][C:3]=1[NH:4][CH2:5][C:6]1[C:7]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][CH2:22][O:23]C3CCCCO3)[CH:16]=2)=[N:8][C:9]([S:12][CH3:13])=[N:10][CH:11]=1.C(N(CC)CC)C.[C:41](Cl)(Cl)=[O:42].[Cl-].[NH4+]>O1CCCC1.C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:33]=[CH:32][CH:31]=[CH:30][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:20]=[CH:19][CH:18]=[C:17]([CH2:21][CH2:22][OH:23])[CH:16]=2)[C:41]1=[O:42]

Participants

7

Reactant 4

HCID 6371PhosgeneHCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 22125057HCID 22125057, compound

Product 1

HCID 22125179HCID 22125179, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2.6 g (4.9 mmol) of 5-(2-bromoanilino)methyl-4-[3-(2-(tetrahydropyranyloxy)ethyl)phenyl]amino-2-methylthiopyrimidine in 40 ml of tetrahydrofuran was treated with 2 ml (14.4 mmol) of triethylamine and the resulting solution added dropwise to an ice-cooled solution of phosgene (3 ml of a 20% solution in toluene, 5.8 mmol) in 40 ml of tetrahydrofuran. After 1 hour 50 ml of a saturated solution of ammonium chloride was added. The mixture was separated and the organic phase dried over magnesium sulfate and filtered. To the solution was added 20 ml of a saturated solution of hydrogen chloride in ethyl acetate. After 10 minutes the solution was evaporated to afford 1.8 g (78%) of 3-(2-bromophenyl)-3,4-dihydro-1-[3-(2-hydroxyethyl)phenyl]-7-methylthio-pyrimido[4,5-d]pyrimidin-2(1H)-one as a white solid. [Mass spectrum (ESI) MH+ =471].

Workup

  1. customThe mixture was separated
  2. dry with materialthe organic phase dried over magnesium sulfate
  3. filtrationfiltered
  4. additionTo the solution was added 20 ml of a saturated solution of hydrogen chloride in ethyl acetate
  5. customAfter 10 minutes the solution was evaporated

Sources & evidence

ORD record
ord-859fb430af574942979500895fba18d6
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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