5-hydroxy-1,3-diazinane-2-thione

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:-10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 26.4 g of tetrahydro-5-hydroxy-2(1H)-pyrimidinethione, 30 ml of ethyl bromide and 250 ml of ethanol was refluxed for 7 hours, clarified, diluted with 250 ml of ether and cooled to -10° C. The solid was crystallized twice from ether, giving 19.5 g of 2-(ethylthio)-1,4,5,6-tetrahydro-5-pyrimidinol, hydrobromide, mp 106°-108° C. was refluxed for 7 hours The solid was crystallized twice from ether

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Using (2R)-2-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-phenylacetic acid and 5-hydroxytetrahydropyrimidine-2(1H)-thion (cf. JP-Hei01 (1989)-128970A), the title compound was prepared by a method similar to Step 2 of Referential Example 12.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Using (2R)-2-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-phenylacetic acid and 5-hydroxytetrahydropyrimidine-2(1H)-thion (cf. JP-Hei01 (1989)-128970A), the title compound was prepared by a method similar to Step 2 of Referential Example 12.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Using (2R)-2-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-phenylacetic acid and 5-hydroxytetrahydropyrimidine-2(1H)-thion (cf. JP-Hei01 (1989)-128970A), the title compound was prepared by a method similar to Step 2 of Referential Example 12.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Using (2R)-2-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-phenylacetic acid and 5-hydroxytetrahydropyrimidine-2(1H)-thion (cf. JP-Hei01 (1989)-128970A), the title compound was prepared by a method similar to Step 2 of Referential Example 12.

Conditions: temp:-10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 26.4 g of tetrahydro-5-hydroxy-2(1H)-pyrimidinethione, 30 ml of ethyl bromide and 250 ml of ethanol was refluxed for 7 hours, clarified, diluted with 250 ml of ether and cooled to -10° C. The solid was crystallized twice from ether, giving 19.5 g of 2-(ethylthio)-1,4,5,6-tetrahydro-5-pyrimidinol, hydrobromide, mp 106°-108° C. was refluxed for 7 hours The solid was crystallized twice from ether

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Using (2R)-2-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-phenylacetic acid and 5-hydroxytetrahydropyrimidine-2(1H)-thion (cf. JP-Hei01 (1989)-128970A), the title compound was prepared by a method similar to Step 2 of Referential Example 12.