Ammonium Chloride → HCID 178445912, compound

HRID 550757Notes

Reaction equation

HRID 550757 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[C:9]([N:10]([CH3:18])[C@H:11]([CH2:14][CH:15]([CH3:17])[CH3:16])[CH2:12][OH:13])=[N:8][C:7]([S:19]CC3C=CC=CC=3)=[N:6][C:5]=2[N:27]=1.[Na].[NH4+].[Cl-]>>[NH2:1][C:2]1[S:3][C:4]2[C:9]([N:10]([CH3:18])[C@H:11]([CH2:14][CH:15]([CH3:17])[CH3:16])[CH2:12][OH:13])=[N:8][C:7]([SH:19])=[N:6][C:5]=2[N:27]=1

Participants

4

Reactant 3

HCID 25517Ammonium ChlorideHCID 5360545SodiumHCID 86613131(2R)-2-[[2-Amino-5-(benzylthio)[1,3]thiazolo[4,5-d]pyrimidin-7-yl](methyl)amino]-4-methylpentan-1-ol

Product 1

HCID 178445912HCID 178445912, compoundYield 80.4%

Procedure

A three-neck round-bottomed flask was immersed in a dry ice/ethanol cooling bath and equipped with a dry ice/ethanol condenser. The system was flushed with nitrogen and ammonia (approximately 50 mL) was condensed into the flask. (2R)-2-[[2-Amino-5-(benzylthio)[1,3]thiazolo[4,5-d]pyrimidin-7-yl](methyl)amino]-4-methylpentan-1-ol (1 g, 2.5 mmol) was added to the flask, resulting in a clear yellow solution. Small pieces of sodium metal (size 2-3 mm) were added one by one to the reaction mixture. When a persistent blue colour (>20 sec) appeared, a spoon of solid NH4Cl was added to quench the reaction. The ammonia was evaporated off. Water (50 mL) was added and the mixture was neutralized with 1M HCl (aq.) to pH 7. The precipitated yellow solid was collected by filtration, washed with water and dried in vacuo to yield 630 mg of the title compound (80% yield).

Workup

  1. customA three-neck round-bottomed flask was immersed in a dry ice/ethanol cooling bath
  2. customequipped with a dry ice/ethanol condenser
  3. customThe system was flushed with nitrogen and ammonia (approximately 50 mL)
  4. customcondensed into the flask
  5. customresulting in a clear yellow solution
  6. customa persistent blue colour (>20 sec)
  7. customto quench
  8. customthe reaction
  9. customThe ammonia was evaporated off
  10. additionWater (50 mL) was added
  11. filtrationThe precipitated yellow solid was collected by filtration
  12. washwashed with water
  13. customdried in vacuo

Sources & evidence

ORD record
ord-4e0736c05da849ce8deb6f38fe816cc1
Source dataset
uspto-grants-2011_05
Patent number
US07947693B2

Reaction notes

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