Triethylamine → HCID 53971714, compound

HRID 845117Notes

Reaction equation

HRID 845117 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1([CH2:9][NH2:10])[CH2:8][CH2:7]1.[Cl:11][CH2:12][C@H:13]1[O:17][C@@H:16]([N:18]2[C:37]3[N:36]=[CH:35][N:34]=[C:22](NCC4(C5C=CC=CC=5)CC4)[C:21]=3[N:20]=[CH:19]2)[C@H:15]([OH:38])[C@@H:14]1[OH:39].C(N(CC)CC)C>C(O)=O>[Cl:11][CH2:12][C@H:13]1[O:17][C@@H:16]([N:18]2[C:37]3[N:36]=[CH:35][N:34]=[C:22]([NH:10][CH2:9][C:6]4([C:2]5[S:1][CH:5]=[CH:4][CH:3]=5)[CH2:8][CH2:7]4)[C:21]=3[N:20]=[CH:19]2)[C@H:15]([OH:38])[C@@H:14]1[OH:39]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 156111751-[1-(Thiophen-2-yl)cyclopropyl]methanamineHCID 53967354HCID 53967354, compound

Product 1

HCID 53971714HCID 53971714, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

(1-Thien-2-ylcyclopropyl)methylamine (0.55 g, 3.6 mmol), see Example 3, 6-chloropurine-5'-deoxy-5'-chlororiboside-2',3'-isopropylidene (1.25 g, 3.6 mmol, as prepared in Example 5) and triethylamine (0.75 g, 7.5 mmol) are reacted together as described in Example 5. Aqueous formic acid hydrolysis gives 5'-chloro-5'-deoxy-N6-((1-thien-2-ylcyclopropyl)methyl)adenosine (0.44 g, 29%) as a light khaki solid foam m.p. 69°-75° C. Found: C, 50.53; H, 4.90; N, 15.90; Cl, 9.13; S, 7.22%. C18H20ClN5O3S calculated requires: C, 51.25; H, 4.74; N, 16.61; Cl, 8.42; S, 7.59%.

Workup

  1. customare reacted together

Sources & evidence

ORD record
ord-d033ab34bd4a4e5ebb1938b46eb2c994
Source dataset
uspto-grants-1988_07
Patent number
US04755594

Reaction notes

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