Sodium Hydroxide → 7-Amino-2-chlorothiazolo[4,5-d]pyrimidine

HRID 2248937Notes

Reaction equation

HRID 2248937 reaction equation
N[C:2]1[S:3][C:4]2[C:9]([NH2:10])=[N:8][CH:7]=[N:6][C:5]=2[N:11]=1.[OH-].[Na+].N([O-])=O.[Na+].[Li+].[Cl-:19]>O>[NH2:10][C:9]1[C:4]2[S:3][C:2]([Cl:19])=[N:11][C:5]=2[N:6]=[CH:7][N:8]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 433294Lithium ChlorideHCID 10953913Thiazolo[4,5-d]pyrimidine-2,7-diamineHCID 23668193Sodium Nitrite

Product 1

HCID 145057597-Amino-2-chlorothiazolo[4,5-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Conditions

Temperature
45 °C

Procedure

To a suspension of 2,7-diaminothiazolo[4,5-d]pyrimidine (27: 16.3 g, 97.3 mmol) in water (200 mL) at 55° C. was added enough 1N NaOH (about 100 mL) to dissolve the starting material and sodium nitrite (8.0 g) was then added. This solution was then added dropwise over 30 min. to a solution containing con HC1 (400 mL), water (100 mL) and LiCl (60 g) at 30° C. The resulting mixture was warmed to 45° C. for 15 min. and then hot water (1 L, 90°) was added. The reaction mixture was stirred overnight at room temperature, filtered to remove unreacted starting material and the filtrate was neutralized with solid NaOH to pH 4. The resulting solid was filtered off, washed with water and dried to yield 28: 5.38 g, 34%: recrystallization from water gave an analytical sample: mp>234° C. decomp.: UV λmax (pH 1) 228 nm (ε), 296 () UV λmax (pH 7) 232 nm (ε), 298 (): UV λmax (pH 11) 227 nm (ε), 300 (): 1H NMR (DMSO-d6) δ 7.82 (b, 2H, NH2, exchanges with D2O), 8.41 (s, 1H, C5H). Anal. Calcd. for C5H3N4SC1.0.1H2O: C, 31.87: H, 1.71: N, 29.74: S, 17.02: C1, 18.82. Found: C, 31.71: H, 1.50: N, 29.35: S, 16.92: C1, 19.54.

Workup

  1. additionwas then added
  2. additionThis solution was then added dropwise over 30 min. to a solution
  3. filtrationfiltered
  4. customto remove unreacted
  5. filtrationThe resulting solid was filtered off
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-fbafa5d9544941739a6e263362017b9e
Source dataset
uspto-grants-1991_08
Patent number
US05041426

Reaction notes

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