Water → 7-(2-Chloro-6-fluorobenzylamino)[1,2,5]thiadiazolo[3,4-d]pyrimidine

HRID 1704778

Reaction equation

HRID 1704778 reaction equation
[NH2:1][C:2]1[C:3]2[C:4](=[N:8][S:9][N:10]=2)[N:5]=[CH:6][N:7]=1.[Cl:11][C:12]1[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[C:13]=1[CH2:14]N.O.CCCCCC>C(Cl)(Cl)Cl.CO>[Cl:11][C:12]1[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[C:13]=1[CH2:14][NH:1][C:2]1[C:3]2[C:4](=[N:8][S:9][N:10]=2)[N:5]=[CH:6][N:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8058HexaneHCID 848332-Chloro-6-fluorobenzylamineHCID 95769(1,2,5)Thiadiazolo(3,4-d)pyrimidin-7-amine

Product 1

HCID 204820257-(2-Chloro-6-fluorobenzylamino)[1,2,5]thiadiazolo[3,4-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Conditions

Temperature
105 °C

Procedure

A flask was charged with 1.54 g. (0.01 mole) of 7-amino[1,2,5]thiadiazolo[3,4-d]pyrimidine prepared by the process set forth in Example 1 and 4.0 g. (0.025 mole) of 2-chloro-6-fluorobenzylamine prepared by the process set forth in Example 2. The suspension was stirred and heated at 105° C. for 18 hours. Ten ml. water and 20 ml. hexane were added in one portion and the resulting solid collected by filtration. The cake was washed with hexane and dried at 50° C. in vacuo to afford 2.86 g. (97%) of product. M.p. 224°-226° C.; tlc on silica gel in chloroform-methanol (8:1) showed a single fluorescent blue spot at Rf = 0.8; NMR (DMSO-d6) δ 4.92 (2H, s); 7.21 (broad s, 3H); 8.44 (s, 1H); 9.45 (s, 1H).

Workup

  1. additionA flask was charged with 1.54 g
  2. filtrationthe resulting solid collected by filtration
  3. washThe cake was washed with hexane
  4. customdried at 50° C. in vacuo
  5. customto afford 2.86 g

Sources & evidence

ORD record
ord-56f1b9adde13466f9990db05be279ecb
Source dataset
uspto-grants-1978_11
Patent number
US04127721

Linked notes

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