HCID 178479710, compound → 2-Chloro-5,6,7,8,9,10-hexahydrocycloocta[d]pyrimidine

HRID 252916Notes

Reaction equation

HRID 252916 reaction equation
[N:1]1[C:2](=O)[NH:3][CH:4]=[C:5]2[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:6]=12.O(Cl)[Cl:15].[P+3]>>[Cl:15][C:2]1[N:3]=[CH:4][C:5]2[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[N:1]=1

Participants

3

Reactant 2

HCID 178479710HCID 178479710, compoundHCID 178517333HCID 178517333, compound

Product 1

HCID 581995242-Chloro-5,6,7,8,9,10-hexahydrocycloocta[d]pyrimidine

Procedure

Crude 5,6,7,8,9,10-Hexahydrocycloocta[d]pyrimidin-2(3H)-one was heated in phosphorus (III) oxychloride (50 mL) for 1.75 h. The solvent was removed under vacuum and the residue was treated with ice water and 1M aqueous potassium carbonate solution, the aqueous layer was extracted with a mixture of diethyl ether and ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under vacuum to give 2-chloro-5,6,7,8,9,10-hexahydrocycloocta[d]pyrimidine as a yellow solid, 1.5 g; 1H NMR (CDCl3, 300 MHz) 8.18 (s, 1H), 2.82 (m, 2H), 2.66 (m, 2H), 1.74 (m, 2H), 1.61 (m, 2H), 1.34 (m, 4H) ppm; 13C NMR (CDCl3, 75 MHz) 173.25, 158.66 (2C), 132.74, 34.28, 32.03, 30.20, 28.57, 26.02, 25.90; MS (ES) 197/199 (M+H).

Workup

  1. customThe solvent was removed under vacuum
  2. additionthe residue was treated with ice water and 1M aqueous potassium carbonate solution
  3. extractionthe aqueous layer was extracted with a mixture of diethyl ether and ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-031a20be0f8544ae9cbccbbcc37b76fb
Source dataset
uspto-grants-2011_01
Patent number
US07872000B2

Reaction notes

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