Hydrochloric Acid → 7-Amino-2-chlorothiazolo[4,5-d]pyrimidine

HRID 1638533ノート

反応式

HRID 1638533 の反応式
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+].[ClH:18].[Li+].[Cl-]>O>[NH2:10][C:9]1[C:4]2[S:3][C:2]([Cl:18])=[N:11][C:5]=2[N:6]=[CH:7][N:8]=1

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 433294Lithium ChlorideHCID 10953913Thiazolo[4,5-d]pyrimidine-2,7-diamineHCID 23668193Sodium Nitrite

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒3 回

反応条件

温度
45 °C

実験手順

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 HCl (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 119 227 nm (ε), 300 (): 1H NMR (DMSO-d6) δ7.82 (b, 2H, NH2, exchanges with D2O), 8.41 (s, 1H, C5H). Anal. Calcd. for C5H3N4SCl.0.1H2O: C, 31.87: H, 1.71: N, 29.74: S, 17.02: Cl, 18.82. Found: C, 31.71: H, 1.50: N, 29.35: S, 16.92: Cl, 19.54.

後処理

  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

出典と根拠

ORDレコード
ord-a228ee3d394c49b0bed9ee9d8d3ef051
出典データセット
uspto-grants-1989_11
特許番号
US04880784

反応ノート

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